Journal of the American Chemical Society p. 7921 - 7925 (1989)
Update date:2022-09-26
Topics:
Fuji, Kaoru
Node, Manabu
Nagasawa, Hideko
Naniwa, Yoshimitsu
Taga, Tooru
et al.
The reactions of chiral nitro enamines 2a-c with zinc enolates 4-6 of α-substituted δ-lactones afforded α,α-disubstituted δ-lactones with a high ee through an addition-elimination process.The best results were obtained with the reaction of 2c with 5.Michael-type addition of the enolate onto the nitro enamine is kinetically controlled and decides the absolute stereochemistry of the product.A cyclic transition model is proposed to rationalize the S-selectivity.
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