The first example of enantioselective allyl transfer from a linear homoallylic alcohol to an aldehyde.
[reaction: see text] The first example of enantioselective linear homoallylic alcohol transfer reaction was revealed. In all cases, the whole rearrangement is thermodynamically favorable and a steric effect is the driving force of this reaction. The preservation of the stereocenter and olefin geometry together with the isolation of gamma-adduct homoallylic alcohols in one isomeric form have warranted the proposed mechanism.
Department of Chemistry, 3 Science Drive 3, National University of Singapore, Singapore 117543. chmlohtp@nus.edu.sg
Teck-Peng
TP
Loh
Chi-Lik
CL
Ken Lee
Kui-Thong
KT
Tan
D000438:Alcohols / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry; D018942:Macrolides; D013237:Stereoisomerism; D000097442:Amphidinolides
D000438:Alcohols; D000447:Aldehydes; D000498:Allyl Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D018942:Macrolides; C409107:amphidinolide K; D000097442:Amphidinolides