[2+2]-photocycloaddition of 1,1-diethoxyethylene to chiral polyfunctional 2-cyclohexenones.: Regioselectivity and π-facial discrimination

被引:14
|
作者
García-Expósito, E
Alvarez-Larena, A
Branchadell, V [1 ]
Ortuño, RM
机构
[1] Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Spain
[2] Univ Autonoma Barcelona, Unitat Cristal Iografia, E-08193 Barcelona, Spain
来源
JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 04期
关键词
D O I
10.1021/jo035532n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The photochemical [2 + 2]-cycloadditions of 1,1-diethoxyethylene to chiral polyfunctional 2-cyclo-hexenones have been carried out leading to the production of highly constrained unusual alpha-amino acids with excellent regioselectivity and satisfactory yields. Theoretical calculations have been done to rationalize the observed regio- and diastereoselectivity and show that regiochemistry is determined by the relative rate of formation of the 1,4-biradical intermediates and not by the stability of these species.
引用
收藏
页码:1120 / 1125
页数:6
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