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催化剂活化和配体空间性质对胺和酚盐对映选择性烯丙基化反应的影响。

Effects of catalyst activation and ligand steric properties on the enantioselective allylation of amines and phenoxides.

作者信息

Leitner Andreas, Shu Chutian, Hartwig John F

机构信息

Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 6520-8107, USA.

出版信息

Org Lett. 2005 Mar 17;7(6):1093-6. doi: 10.1021/ol050029d.

DOI:10.1021/ol050029d
PMID:15760147
Abstract

[reaction: see text] The yields, enantioselectivities, and regioselectivities of the reactions of amines and phenoxides with allylic carbonates in the presence of a metallacyclic iridium catalyst were compared. These data show that both preactivation of the catalyst and the size of the ligand affect the yield, enantioselectivity, and regioselectivity. With the activated catalyst containing a bis-naphthethylamino group, the allylic amination and etherification of a broad range of allylic carbonates occurred in high yields and with high regioselectivities and enantioselectivities.

摘要

[反应:见正文] 比较了在金属环铱催化剂存在下胺和酚盐与烯丙基碳酸酯反应的产率、对映选择性和区域选择性。这些数据表明,催化剂的预活化和配体的大小都会影响产率、对映选择性和区域选择性。使用含有双萘乙氨基的活化催化剂时,多种烯丙基碳酸酯的烯丙基胺化和醚化反应以高收率、高区域选择性和对映选择性发生。

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