外消旋无环α-（烷氧基）烷基铜酸盐和α-（N-氨基甲酰基）烷基铜酸盐的对映选择性反应。

Enantioselective reactions of scalemic acyclic alpha-(alkoxy)alkyl- and alpha-(N-carbamoyl)alkylcuprates.

作者信息

Dieter R Karl, Watson Rhett T, Goswami Rajesh

机构信息

Department of Chemistry, Hunter Laboratory, Clemson University, Clemson, South Carolina 29634-0973, USA.

出版信息

Org Lett. 2004 Jan 22;6(2):253-6. doi: 10.1021/ol036237s.

DOI:10.1021/ol036237s

PMID:14723541

Abstract

[reaction: see text] Scalemic acyclic alpha-(alkoxy)alkyl- and alpha-(N-carbamoyl)alkylcuprates prepared from organostannanes via organolithium reagents react with vinyl iodides, propargyl mesylates, and alpha,beta-enones to afford coupled products with enantioselectivities ranging from 0 to 99% ee depending upon cuprate reagent, substrate structure, solvent, and temperature. In general, lithium cuprates give higher chemical yields and lower enantioselectivities, while the trends are reversed for the corresponding zinc cuprate reagents.

摘要

[反应：见正文] 通过有机锂试剂由有机锡烷制备的无环α-（烷氧基）烷基和α-（N-氨基甲酰基）烷基铜酸盐与乙烯基碘、炔丙基甲磺酸酯和α，β-烯酮反应，根据铜酸盐试剂、底物结构、溶剂和温度，得到对映选择性范围为0至99%ee的偶联产物。一般来说，锂铜酸盐给出更高的化学产率和更低的对映选择性，而相应的锌铜酸盐试剂则趋势相反。