Enantioselective synthesis of (E)-delta-stannyl homoallylic alcohols via aldehyde allylboration using alpha-stannylallylboranes generated by allene hydroboration followed by a highly diastereoselective 1,3-boratropic shift.
A highly enantioselective synthesis of (E)-delta-stannyl homoallylic alcohols 4 via aldehyde allylboration reactions of the double-chiral allylborane reagent 2a is reported. Allylborane 2a was generated from the hydroboration of commercially available allenylstannane 1 with ((d)Ipc)(2)BH at -40 to -20 degrees C followed by a kinetically controlled and highly diastereoselective 1,3-boratropic shift in intermediate 3a.
Chen
Ming
M
Department of Chemistry, Scripps Florida, Jupiter, Florida 33458, USA.
Ess
Daniel H
DH
Roush
William R
WR
D000447:Aldehydes / Q000737:chemistry*; D000466:Alkadienes / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D008562:Membrane Glycoproteins; D008958:Models, Molecular; D008968:Molecular Conformation; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000466:Alkadienes; D001880:Boranes; D008562:Membrane Glycoproteins; D020005:Propanols; C048022:substrate adhesion molecules; C006463:allyl alcohol; C025947:propadiene