Solution structures of the mixed aggregates derived from lithium acetylides and a camphor-derived amino alkoxide

被引：38

作者：

Briggs, TF ^{[1
]}

Winemiller, MD ^{[1
]}

Xiang, BS ^{[1
]}

Collum, DB ^{[1
]}

机构：

[1] Cornell Univ, Baker Lab, Dept Chem & Chem Biol, Ithaca, NY 14853 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 19期

关键词：

D O I：

10.1021/jo010305b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Low-temperature Li-6, C-13, and N-15 NMR spectroscopies reveal that mixtures of lithium cyclopropylacetylide or lithium phenylacetylide (RCCLi) and a vicinal amino alkoxide derived from camphor (R*OLi) in THF/pentane afford an asymmetric (RCCLi)(3)(R*OLi) mixed tetramer and a C-2-symmetric (RCCLi)(2)(R*OLi)(2) mixed tetramer depending on the stoichiometries. The corresponding (RCCLi)(R*OLi)(3) mixed tetramer is not observed. R*OLi-mediated additions of PhCCLi to benzaldehyde proceed with up to an 8:1 enantiomeric ratio that depend on both the choice of R*OLi and the PhCCLi/R*OLi stoichiometries. The results are considered in light of a previously proposed mechanism for the 1,2-addition to a trifluoromethyl ketone.

引用

页码：6291 / 6298

页数：8

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