科研之友
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摘要
The tandem 1,4-addition-aldol condensation reaction of diethylzinc, alpha,beta-unsaturated chiral enantiopure oxazolidines derived from 2-phenylglycinol, and carbonyl compounds is disclosed. The reaction proceeds through a radical-polar crossover mechanism involving the aldol condensation of a trisubstituted zinc enolate through a Zimmerman-Traxler transition state. Installation of a 2pyridine moiety at the hemiaminal position of the chiral auxiliary allows obtaining both excellent asymmetric induction and diastereoselectivity (up to > 90% de). The developed protocol is suitable for aromatic and aliphatic aldehydes, as well as ketones.
- 出版日期2017-1
