1338323-34-4

Basic information

• Product Name: (1R,2R,3S,5R)-2-(benzyloxy)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol
• Synonyms: (1R,2R,3S,5R)-2-(benzyloxy)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol
• CAS NO: 1338323-34-4
• Molecular Weight: 260.376
• Mol File: 1338323-34-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1R,2R,3S,5R)-2-(benzyloxy)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,3S,5R)-2-(benzyloxy)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol(1338323-34-4)
• EPA Substance Registry System: (1R,2R,3S,5R)-2-(benzyloxy)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol(1338323-34-4)

Safety Data

• Hazardous Substances Data: 1338323-34-4(Hazardous Substances Data)

Upstream product

• 7785-26-4 (-)-α-pinene 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 100-39-0 benzyl bromide 

Downstream Products

• 1338323-44-6 C₂₇H₃₁F₃O₄ 
• 1338323-39-9 (1R,2R,3S,5R)-2-(benzyloxy)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl 3,3,3-trifluoropropanoate 

Relevant articles and documents

Enantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning

Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral catalysts remains a challenge and highlights the need to identify new chemotypes for this purpose. Herein, the discovery and optimization of a bench-stable chiral 9-hydroxy-9,10-boroxarophenanthrene catalyst is described and applied in the highly enantioselective desymmetrization of 2-aryl-1,3-diols using benzylic electrophiles under operationally simple, ambient conditions. Nucleophilic activation and discrimination of the enantiotopic hydroxy groups on the diol substrate occurs via a defined chairlike six-membered anionic complex with the hemiboronic heterocycle. The optimal binaphthyl-based catalyst 1g features a large aryloxytrityl group to effectively shield one of the two prochiral hydroxy groups on the diol complex, whereas a strategically placed "methyl blocker"on the boroxarophenanthrene unit mitigates the deleterious effect of a competing conformation of the complexed diol that compromised the overall efficiency of the desymmetrization process. This methodology affords monoalkylated products in enantiomeric ratios equal or over 95:5 for a wide range of 1,3-propanediols with various 2-aryl/heteroaryl groups.

Preparation and application of 2-(arylmethoxy)isopinocampheols for the asymmetric aldol reaction of 3,3,3-trifluoropropionates

The preparation of 2-(arylmethoxy)isopinocampheols from pinanediol via the DIABL-H reduction of the corresponding aryl aldehyde acetals has been described. A systematic examination of the asymmetric aldol reaction of 3,3,3-trifluoropropionates led to the double diastereoselective aldol reaction of 2-(arylmethoxy)isopinocampheyl 3,3,3-trifluoropropionates providing anti-α-trifluoromethyl-β-hydroxy esters in 63-85% yields, ≥99% anti-selectivity and 80-96% de for the anti-isomer.