Remarkable diastereoselectivity in the addition of allylic and unsaturated diorganozinc reagents to beta-(N,N-dialkylamino)-aldehydes.
1,3-Anti amino alcohols 5(a)-18(a) are obtained with high diastereoselectivity by use of diorganozinc reagents in additions to amino aldehydes 2a and 2b. The corresponding Grignard reagents exhibit low to modest diastereoselectivity. The highly diastereoselective zinc-based method makes available a wide range of 4,4-disubstituted cyclohexenone derivatives containing contiguous stereocenters.
Soucy
Regina L
RL
Department of Chemistry, William Marsh Rice University, Houston, Texas 77005-1892, USA.
Kozhinov
Denis
D
Behar
Victor
V