Stereoselective synthesis of gamma-substituted (Z)-allylic boranes via kinetically controlled hydroboration of allenes with 10-TMS-9-borabicyclo[3.3.2]decane.
Kinetically controlled hydroboration of allenes 8 and 14a-d with the readily accessible Soderquist borane 7, which is generated in situ from borohydride 6, constitutes a convenient and preparatively useful method for synthesis of (Z)-gamma-(substituted)allylboranes 9 and 15a-d. These allylboranes undergo highly diastereo- (> or = 90: 10) and enantioselective (typically 89-96% e.e.) allylboration reactions with representative aldehydes to give syn-beta-functionalized homoallylic alcohols.
Kister
Jeremy
J
Department of Chemistry, Scripps Florida, Jupiter, Florida 33458, USA.
DeBaillie
Amy C
AC
Lira
Ricardo
R
Roush
William R
WR
D000466:Alkadienes / Q000737:chemistry*; D000473:Alkanes / Q000737:chemistry*; D000498:Allyl Compounds / Q000138:chemical synthesis*; D001880:Boranes / Q000138:chemical synthesis*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D007700:Kinetics; D013237:Stereoisomerism
D000466:Alkadienes; D000473:Alkanes; D000498:Allyl Compounds; D001880:Boranes; D001643:Bridged Bicyclo Compounds; C025947:propadiene; C012867:decane