Asymmetric Tandem Conjugate Addition-Aldol Condensation with N-Acryloyloxazolidines Derived from 2-Phenylglycinol
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- 作者：Ivá ; n Zelocualtecatl-Montiel ; Dr. Fernando Garcí ; a-Á ; lvarez ; Dr. Jorge R. Juá ; rez ; Dr. Laura Orea ; Prof. Dr. Dino Gnecco ; Dr. Angel Mendoza ; Prof. Dr. Fabrice Chemla ; Dr. Franck Ferreira ; Dr. Olivier Jackowski ; Dr. David M. Aparicio ; Prof. Dr. Alejandro Perez-Luna and Prof. Dr. Joel L. Terá ; n
- 刊名：Asian Journal of Organic Chemistry
- 出版年：2017
- 出版时间：January 2017
- 年：2017
- 卷：6
- 期：1
- 页码：67-70
- 全文大小：985K
- ISSN：2193-5815
文摘
The tandem 1,4-addition–aldol condensation reaction of diethylzinc, α,β-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 2-pyridine 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.