856676-11-4

Basic information

• Product Name: (-)-9-(1R,2R-Pseudoephedrinyl)-(10S)-(trimethylsilyl)-9-borabicyclo[3.3.2]decane
• Synonyms: (-)-9-(1R,2R-Pseudoephedrinyl)-(10S)-(trimethylsilyl)-9-borabicyclo[3.3.2]decane
• CAS NO: 856676-11-4
• Molecular Formula: C₂₂H₃₈BNOSi
• Molecular Weight: 371.43972
• Product Categories: Allylation;Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents
• Mol File: 856676-11-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 135-148 °C
• Appearance: /
• CAS DataBase Reference: (-)-9-(1R,2R-Pseudoephedrinyl)-(10S)-(trimethylsilyl)-9-borabicyclo[3.3.2]decane(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-9-(1R,2R-Pseudoephedrinyl)-(10S)-(trimethylsilyl)-9-borabicyclo[3.3.2]decane(856676-11-4)
• EPA Substance Registry System: (-)-9-(1R,2R-Pseudoephedrinyl)-(10S)-(trimethylsilyl)-9-borabicyclo[3.3.2]decane(856676-11-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 856676-11-4(Hazardous Substances Data)

Upstream product

• 321-97-1 (1R,2R)-pseudoephedrine 
• 1161746-29-7 C₂₁H₄₁BO₂Si 
• 1161746-27-5 C₂₀H₃₉BO₂Si 
• 848617-93-6 (+/-)-B-methoxy-10-trimethylsilyl-9-borabicyclo[3.3.2]decane 
• 6224-91-5 trimethyl(prop-1-ynyl)silane 
• 872359-60-9 (S)-10-Trimethylsilanyl-9-(3-trimethylsilanyl-prop-2-ynyl)-9-bora-bicyclo[3.3.2]decane 
• 872359-59-6 (R)-10-Trimethylsilanyl-9-(3-trimethylsilanyl-prop-2-ynyl)-9-bora-bicyclo[3.3.2]decane 
• 872359-77-8 (R)-9-[(S)-1-((E)-Propenyl)-2-trimethylsilanyl-buta-2,3-dienyloxy]-10-trimethylsilanyl-9-bora-bicyclo[3.3.2]decane 
• 856675-97-3 (+)-(10S)-B-methoxy-10-trimethylsilyl-9-borabicyclo[3.3.2]decane 

Downstream Products

• 856675-86-0 (S)-9-((S)-1-Phenyl-but-3-enyloxy)-10-trimethylsilanyl-9-bora-bicyclo[3.3.2]decane 
• 173654-27-8 (+)-(1R)-1-phenyl-2-(trimethylsilyl)-2,3-butadien-1-ol 
• 872359-60-9 (S)-10-Trimethylsilanyl-9-(3-trimethylsilanyl-prop-2-ynyl)-9-bora-bicyclo[3.3.2]decane 
• 321-97-1 (1R,2R)-pseudoephedrine 

Relevant articles and documents

Asymmetric γ-methoxyallylation with the robust 10-tms-9- borabicyclo[3.3.2]decanes

The asymmetric γ-methoxyallylboration of aldehydes with the configurationally very stable 1 gives nonracemic threo-β-methoxyhomoallylic alcohols 7 (65-93%) with excellent selectivity (96-99% de, 98-99% ee). The corresponding homoallylic amines 10 are obta

Asymmetric allyl- and crotylboration with the robust, versatile, and recyclable 10-TMS-9-borabicyclo[3.3.2]decanes

The remarkable versatility and selectivity of the 10-(trimethylsilyl)-9- borabicyclo[3.3.2]decanes (10-TMS-9-BBDs) in the allyl- and crotylboration of representative aldehydes are reported. The new reagents are prepared through air-stable crystalline pseudoephedrine borinic ester complexes of the 10-TMS-9-BBDs (4), which are available in 63% overall yield from B-MeO-9-BBN through a simple two-step procedure. These complexes 4 are directly converted to the corresponding B-allyl-10-TMS-9-BBDs (1) with allylmagnesium bromide, which either can be isolated (98%) or used in situ for the allylations. The remarkable enantioselectivity (96 to ≥99% ee) of these reagents in the rapid (3 h), asymmetric allylboration process at -78 °C is only slightly diminished when it is conducted at 25 °C, a phenomenon attributable to its rigid bicyclic structure. In addition to providing the homoallylic alcohols 6 efficiently (68-80%), the procedure also permits the efficient recovery of 4 (68-84%) for the direct regeneration of 1. Alternatively, an oxidative workup procedure can be used for the preparation of 6. The reagent gives predictable stereochemistry and exhibits an extremely high level of reagent control in the allylboration of D-glyceraldehyde acetonide. A simple and efficient procedure has been developed for the preparation of all four geometric and enantiomeric isomers of the B-crotyl-10-TMS-9-BBDs (10) from optically pure enantiomers of B-MeO-10-TMS-9-BBD (3). These reagents 10 also add rapidly (3 h) and efficiently to representative aldehydes at -78 °C, providing ready access to all four of the possible stereoisomers of the β-methyl homoallylic alcohols 12-15 (69-92%) in high dr (≥98:2) and ee (94-99%).