22497-08-1

Usage

Type of compound

Alcohol

Derived from

Bicyclic hydrocarbons

Common uses

Synthesis of pharmaceuticals and agrochemicals

Known for

Unique bicyclic structure

Distinct properties

Reactivity due to the bicyclic structure

Use as a reagent

Organic chemistry reactions, particularly in the formation of carbon-carbon bonds

Role in production

Chiral building block for various chemical intermediates

Contribution to stability

Bicyclic structure

Value in development

A valuable component in the development of new materials and compounds

InChI:InChI=1/C10H16O/c1-10(2,11)9-6-7-3-4-8(9)5-7/h3-4,7-9,11H,5-6H2,1-2H3

Upstream product

• 75-11-6 diiodomethane 
• 824-60-2 2-acetyl-5-norbornene 
• 917-64-6 methyl magnesium iodide 
• 542-92-7 cyclopenta-1,3-diene 
• 2903-75-5 (1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 
• 917-54-4 methyllithium 

Relevant academic research and scientific papers

N-alkoxyacrylamides as substrates for enantioselective Diels-Alder reactions

Matrix presented The use of N-alkoxyacrylamides as substrates for Lewis acid catalyzed Diels-Alder reactions has been examined. Enantioselectivities up to 92% ee have been achieved using very simple chiral Lewis acids prepared from triisobutylaluminum and 2,2-dimethyl-α,α,α′,α′-tetra-1-naphthalenyl- TADDOL (1-NaphtTADDOL). The use of Yamamoto's Zn-BINOL, easily prepared from Et2Zn and 1,1′-bi-2-naphthol (BINOL), proved to be even more efficient, and enantioselectivities up to 96% ee were achieved.

Enantioselective Diels-Alder reactions with N-hydroxy-N-phenylacrylamide

Matrix presented The use of hydroxamic acids as templates for Lewis acid catalyzed enantioselective Diels-Alder reactions has been examined. A very simple chiral Lewis acid, prepared by mixing optically pure binaphthol with 3 equiv of trimethylaluminum, catalyzes the [4 + 2] cycloaddition of N-hydroxy-N-phenylacrylamide with cyclopentadiene at 0°C in high yield (>96%) and with a fairly good level of enantioselectivity (91% ee). Facile conversion of the products to the corresponding alcohols or aldehydes makes the hydroxamic acid intermediates particularly useful.

Diastereoselective silacyclopropanations of functionalized chiral alkenes

Lithium reduction of di-tert-butyldichlorosilane and thermal silylene transfer (105-125 °C) are complementary methods for the highly diastereoselective silacyclopropanations of a range of functionalized chiral olefins to afford complex silacycles. We have

NEW POSSIBILITIES FOR CONTROL OF THE TRANSANNULAR CYCLIZATION OF 1,5-DIENES IN THE RITTER REACTION AS ILLUSTRATED BY METHYL-CIS-BICYCLONONA-3,7-DIENES

In the Ritter reaction 3-methyl and 3,4-dimethyl-cis-bicyclonona-3,7-dienes are converted either exclusively into acetylamines having the initial structure or into transannular cyclization products of the tricyclo3,7>nonane (brex