DIASTEREOSELECTIVE ALKYLATION OF 8-PHENYLMENTHYL PHENYLACETATE - AGGREGATED LITHIUM ENOLATE VERSUS NAKED ENOLATE

被引：45

作者：

SOLLADIECAVALLO, A

CSAKY, AG

GANTZ, I

SUFFERT, J

机构：

[1] Laboratoire de Stéréochimie Organométallique, EHICS, 67008 Strasbourg

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 18期

关键词：

D O I：

10.1021/jo00097a041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It is shown that monoalkylation of 8-phenylmenthyl phenylacetate using lithiated bases leads to poor or no diastereoselectivities (50/50 to 69/31) and high yields (75 to 98%) while alkylation using tBu-P4 (a strong and cation free base, known to provide ''naked'' anion) leads to high diastereoselectivities (92/8 to 98/2) and high yields (65 to 95%). It is postulated that, in the case of phenylacetates, the degree of aggregation of the lithium enolate is responsible of the poor diastereoselectivities.

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页码：5343 / 5346

页数：4

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