64234-27-1

Usage

Uses

Used in Organic Synthesis:
[(1R,2S,3R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-3-yl]borane is used as a reagent in organic synthesis for its ability to add a boron atom to unsaturated organic compounds. This makes it a valuable tool in the synthesis of complex organic molecules, as it can facilitate various chemical reactions, including reduction and hydroboration reactions.
Used in Chemical Reactions:
In the Chemical Reactions industry, [(1R,2S,3R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-3-yl]borane is used as a highly reactive compound for a variety of chemical reactions. Its unique structure and reactivity make it an important tool in facilitating reduction and hydroboration reactions, which are essential in the synthesis of complex organic molecules.

Upstream product

• 7785-70-8 (+)-α-pinene 
• 7785-70-8 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 

Downstream Products

• 75420-45-0 (S)-(+)-3-methyl-4-penten-1-ol 
• 75420-44-9 (-)-(3R)-methyl-4-penten-1-ol 
• 88947-07-3 (1S,2S)-trans-isopinocampheyl-(2-methylcyclohexyl)borane 
• 83681-53-2 (1R,2R)-(-)-ethyl trans-(2-methylcyclohexyl)-n-pentylborinate 
• 83681-54-3 (1R,2R)-(-)-ethyl trans-(2-phenylcyclopentyl)ethylborinate 
• 217079-80-6 C₁₉H₃₂BCl 
• 7785-70-8 (+)-α-pinene 
• 681247-31-4 N-[(7S,8S)-1-bromo-7-hydroxy-8-methyl-5,6,7,8-tetrahydro-2-naphthalenyl]-2-fluorobenzenesulfonamide 

Relevant academic research and scientific papers

An Enantioconvergent and Concise Synthesis of Lasonolide A

Efficient access to medicinally significant natural products is an essential basis for the development of pharmaceuticals. The limited availability of marine natural products impedes broad biological evaluation. Despite several elegant syntheses of (?)-lasonolide A having been reported, a practical synthesis of this potent anticancer polyketide remains elusive. Based on the application of borane as a traceless protecting group and the development of an unprecedented bissulfone reagent for Julia olefination, (?)-lasonolide A was assembled in an enantioconvergent manner through the application of stereoselective hydroboration, allylation, and oxidation. This concise route may provide a realistic solution for accessing derivatives and analogues.

Development of Enantiospecific Coupling of Secondary and Tertiary Boronic Esters with Aromatic Compounds

The stereospecific cross-coupling of secondary boronic esters with sp2 electrophiles (Suzuki-Miyaura reaction) is a long-standing problem in synthesis, but progress has been achieved in specific cases using palladium catalysis. However, related couplings with tertiary boronic esters are not currently achievable. To address this general problem, we have focused on an alternative method exploiting the reactivity of a boronate complex formed between an aryl lithium and a boronic ester. We reasoned that subsequent addition of an oxidant or an electrophile would remove an electron from the aromatic ring or react in a Friedel-Crafts-type manner, respectively, generating a cationic species, which would trigger 1,2-migration of the boron substituent, creating the new C-C bond. Elimination (preceded by further oxidation in the former case) would result in rearomatization giving the coupled product stereospecifically. Initial work was examined with 2-furyllithium. Although the oxidants tested were unsuccessful, electrophiles, particularly NBS, enabled the coupling reaction to occur in good yield with a broad range of secondary and tertiary boronic esters, bearing different steric demands and functional groups (esters, azides, nitriles, alcohols, and ethers). The reaction also worked well with other electron-rich heteroaromatics and 6-membered ring aromatics provided they had donor groups in the meta position. Conditions were also found under which the B(pin)- moiety could be retained in the product, ortho to the boron substituent. This protocol, which created a new C(sp2)-C(sp3) and an adjacent C-B bond, was again applicable to a range of secondary and tertiary boronic esters. In all cases, the coupling reaction occurred with complete stereospecificity. Computational studies verified the competing processes involved and were in close agreement with the experimental observations.

BICYCLIC COMPOUNDS

Disclosed are compounds of Formula (I) and/or a salt thereof; wherein R is —OH or —OP(O)(OH)2. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.