(11bS)-Octahydro TRIP Phosphoric Acid FAQ | Aladdin

(11bS)-8,9,10,11,12,13,14,15-Octahydro-4-hydroxy-2,6-bis[2,4,6-tris(1-methylethyl)phenyl]-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin is a chiral phosphoric acid belonging to the TRIP family, widely employed as a Brønsted acid organocatalyst for enantioselective transformations in synthetic chemistry.

SKU

B300943

IUPAC Name

(11bS)-8,9,10,11,12,13,14,15-Octahydro-4-hydroxy-2,6-bis[2,4,6-tris(1-methylethyl)phenyl]-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin

Compound Class

Chiral Brønsted acid phosphoric acid (TRIP analogue, partially saturated backbone)

Core Scaffold

Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin (partially hydrogenated BINAP-phosphate framework)

Stereocentre Configuration

(11bS) — single defined stereocentre conferring axial chirality

Primary Application

Asymmetric organocatalysis: Mannich reactions, transfer hydrogenation, Pictet–Spengler cyclisations, and related enantioselective processes

Storage Recommendation

Store under inert atmosphere, cool and dry, away from moisture and light

What Is This Compound and Why Does It Matter?

(11bS)-8,9,10,11,12,13,14,15-Octahydro-4-hydroxy-2,6-bis[2,4,6-tris(1-methylethyl)phenyl]-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin (Aladdin SKU B300943) is a member of the chiral phosphoric acid (CPA) catalyst family derived from the BINAP/BINOL-phosphate platform. The compound features a partially saturated (octahydro) dinaphtho-dioxaphosphepin backbone bearing two sterically demanding 2,4,6-triisopropylphenyl (TRIP) aryl substituents at the 3,3'-positions, and an (11bS) stereocentre that encodes axial chirality.

Chiral phosphoric acids of this type function as bifunctional Brønsted acid catalysts, capable of simultaneously activating electrophiles through hydrogen-bond donation and orienting nucleophiles through the pendant phosphoryl oxygen. The octahydro modification partially saturates the fused ring system relative to the fully aromatic TRIP catalyst, potentially altering the three-dimensional chiral pocket and electronic properties of the acidic P–OH group, making this compound a valuable structural variant for catalyst optimisation studies.

Key Chemical Properties and Structural Features

The dioxaphosphepin ring system fuses two naphthalene-derived units through a phosphate bridge, creating a rigid C2-symmetric-like chiral environment around the phosphorus atom. The 2,4,6-triisopropylphenyl groups at the 3,3'-positions provide substantial steric shielding of the catalytic site, a design feature known to enforce high enantioselectivity by restricting the approach trajectory of reacting partners.

The P–OH group (formal oxidation state P(V), with the 4-oxide notation indicating the phosphoryl oxygen) is the active Brønsted acidic site. In catalytic cycles the phosphate anion generated upon proton transfer typically remains ion-paired with the substrate-derived cation, serving as a chiral counterion that transmits stereochemical information. The partial saturation of the backbone (octahydro) distinguishes this catalyst from the classical fully-aromatic TRIP phosphoric acid and may subtly modulate conformational flexibility and the depth or shape of the chiral pocket.

Note for researchers: Exact molecular weight, melting point, optical rotation, and measured purity specifications for B300943 should be confirmed from the current Aladdin product datasheet, as these values are subject to lot-specific variation.

Applications in Asymmetric Catalysis

Chiral phosphoric acids of the TRIP class are among the most broadly applied organocatalysts in modern synthetic chemistry. Established reaction classes include:

• Asymmetric Mannich reactions — activation of iminium ions derived from aldehydes or ketones with amines, providing chiral β-amino carbonyl compounds with high ee.
• Transfer hydrogenation of imines — using Hantzsch ester or benzothiazoline as hydride source under CPA catalysis to furnish chiral amines.
• Pictet–Spengler cyclisations — enantioselective construction of tetrahydro-β-carboline and isoquinoline scaffolds relevant to alkaloid synthesis.
• Friedel–Crafts type reactions — CPA-catalysed additions of electron-rich arenes or heterocycles to activated electrophiles.
• Aza-Diels–Alder and related cycloadditions — organocatalytic construction of chiral N-containing ring systems.

The octahydro variant B300943 may be particularly useful in catalyst screening campaigns where the canonical TRIP catalyst does not deliver optimal enantioselectivity, offering a complementary chiral environment through backbone modification.

Handling, Storage, and Safety Guidance

As with most chiral phosphoric acid catalysts, B300943 should be handled with standard laboratory precautions:

• Storage: Store in a tightly sealed container under an inert atmosphere (nitrogen or argon) at low temperature (2–8 °C recommended) in a dry environment, protected from light and moisture. Prolonged exposure to air or moisture may cause hydrolysis of the P–OH functionality or epimerisation.
• Handling: Use in a well-ventilated fume hood. Wear appropriate PPE including gloves, safety glasses, and lab coat. Avoid generating dust during weighing operations.
• Solubility: Typical CPA catalysts of this class are soluble in common organic solvents such as dichloromethane, toluene, chloroform, and THF. Confirm solubility in specific solvents experimentally before use in reactions.
• Stability: The compound is expected to be stable under standard laboratory conditions when stored correctly; however, verify current lot stability data via the Aladdin product datasheet or Safety Data Sheet (SDS).

Always consult the product SDS for complete hazard and disposal information before use.

Ordering and Product Information

This compound is available from Aladdin Scientific under SKU B300943. When ordering, researchers and procurement teams should note the following:

• Quantity options: Please check the current Aladdin website or contact our technical sales team for available pack sizes and pricing.
• Purity grade: Confirm the purity specification on the current product page or certificate of analysis (CoA). For asymmetric catalysis applications, high purity (typically ≥95% or as stated on CoA) and high enantiopurity are critical; always verify ee or optical rotation data on the CoA.
• Lead time: Availability and lead times may vary. Contact Aladdin customer service for current stock status.
• Certificates: A Certificate of Analysis (CoA) and Safety Data Sheet (SDS) are available upon request or via the product page on the Aladdin website.
• Returns and quality issues: In the event of a quality concern, please contact Aladdin customer service with the lot number and CoA for prompt resolution in accordance with our returns policy.

Frequently asked questions

What type of catalyst is (11bS)-Octahydro-TRIP phosphoric acid and how does it work?

It is a chiral Brønsted acid organocatalyst belonging to the TRIP-class chiral phosphoric acid (CPA) family. The P–OH group donates a proton to activate electrophilic substrates (e.g., iminium ions), while the phosphoryl oxygen simultaneously acts as a hydrogen-bond acceptor to orient the nucleophile, creating a well-defined chiral environment that governs facial selectivity and enantioselectivity in the reaction.

How does the octahydro (partially saturated) version differ from the standard fully aromatic TRIP phosphoric acid catalyst?

The octahydro modification partially saturates the fused dinaphtho ring backbone, which can alter the three-dimensional shape of the chiral pocket, the conformational flexibility of the catalyst scaffold, and potentially the pKa of the P–OH group relative to the fully aromatic analogue. These structural differences make B300943 a useful complement to standard TRIP in catalyst screening, particularly for substrate classes where the aromatic catalyst gives suboptimal enantioselectivity. Researchers should experimentally evaluate both variants to identify the optimal catalyst for their specific transformation.

What are the recommended storage conditions for B300943 to maintain its integrity and enantiopurity?

B300943 should be stored in a tightly sealed container under an inert atmosphere (nitrogen or argon) at low temperature (2–8 °C) in a dry, dark location. Exposure to moisture can hydrolyse the phosphoric acid moiety, and prolonged exposure to air or elevated temperatures may compromise enantiopurity. Always verify current storage recommendations on the Aladdin product datasheet or SDS for the specific lot received.

In which reaction types has this class of chiral phosphoric acid catalyst been most commonly applied?

TRIP-class chiral phosphoric acid catalysts have been widely applied in asymmetric Mannich reactions, transfer hydrogenation of imines using Hantzsch esters, Pictet–Spengler cyclisations, Friedel–Crafts additions of electron-rich heterocycles to electrophiles, and aza-Diels–Alder cycloadditions, among others. The specific performance of the octahydro variant B300943 in each of these reaction classes should be evaluated experimentally.

How can I obtain a Certificate of Analysis or Safety Data Sheet for B300943?

A Certificate of Analysis (CoA) and Safety Data Sheet (SDS) for B300943 are available through the Aladdin Scientific product page on our website or by contacting our customer service team directly with your lot number. We recommend always reviewing the CoA for lot-specific purity and enantiopurity data before use in asymmetric catalysis experiments.

References

1. Akiyama, T. Stronger Brønsted Acids. Chemical Reviews, 2007. (Foundational review of chiral phosphoric acid organocatalysis including TRIP-class catalysts.)
2. Terada, M. Chiral Phosphoric Acids as Versatile Catalysts for Enantioselective Transformations. Synthesis, 2010. (Review of BINOL-derived chiral phosphoric acid catalysts and their applications.)
3. Aladdin Scientific product datasheet for B300943: (11bS)-8,9,10,11,12,13,14,15-Octahydro-4-hydroxy-2,6-bis[2,4,6-tris(1-methylethyl)phenyl]-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin. (Source for lot-specific purity, physical data, and storage conditions.)

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.