THE ASYMMETRIC-SYNTHESIS OF 2,2-DIALKYL CARBOXYLIC ESTERS AND 2,2-DISUBSTITUTED DIHYDRONAPHTHALENES

被引：16
|
作者：
MEYERS, AI
WALLACE, RH
HARRE, M
GARLAND, R
机构：
[1] Department of Chemistry, Colorado State University, Fort Collins
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 10期
关键词：
D O I：
10.1021/jo00297a032
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The bicyclic lactams derived from (S)-valinol and 3-benzoylpropionic acid or levulinic acid are useful chiral precursors to the title compounds. Metalation of bicyclic lactams 1 or 4 and alkylation followed by acidic hydrolysis leads to racemic 2-alkyl carboxylic acids. However, sequential metalation-alkylation to 2,2-dialkyl bicyclic lactams 2 and 5 furnishes these systems with good diastereoselectivity. Treatment of 5 with triflic acid causes a facile rearrangement to the oxazolines 7 and hydrolysis leads to the carboxylic esters. Under certain conditions, hydrolysis leads directly to naphthalenes 11. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码：3137 / 3143
页数：7
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