ASYMMETRIC-SYNTHESIS OF 2,3-DISUBSTITUTED SUCCINATES VIA CHIRAL OXAZOLIDINONE CONTROLLED DISPLACEMENT OF ALPHA-TRIFLUOROMETHANESULFONATE SUBSTITUTED ESTERS

被引:22
作者
DECICCO, CP
NELSON, DJ
CORBETT, RL
DREABIT, JC
机构
[1] Chemical and Physical Sciences, Dupont Merck Pharmaceutical Company, Wilmington, Delaware 19880, Experimental Station
关键词
D O I
10.1021/jo00120a022
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The addition of chiral imides to alpha-trifluoromethanesulfonate esters gave chiral 2,3-disubstituted succinates with moderate to excellent diastereoselectivity and in good overall chemical yields. Both syn and anti chiral products are attainable via this methodology, with generally better diastereoselectivity and chemical yields observed in the production of the syn products. The reactions proceed through the predicted S(N)2 displacement of the triflate leaving group, as inferred from the absolute configuration of the products.
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页码:4782 / 4785
页数:4
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