THE STEREOSELECTIVE CONSTRUCTION OF (Z)-3-ARYL-2-FLUOROALKENOATES

被引:50
作者
WELCH, JT
HERBERT, RW
机构
[1] Department of Chemistry, University at Albany, State University of New York, Albany
关键词
D O I
10.1021/jo00303a003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
: The use of 2,4,6-trimethylphenyl a-silyl-a-fluoroacetate in the Peterson olefination reaction leads to the highly stereoselective formation of (Z)-3-aryl-2-fluoroalkenoates via an aldol reaction most likely proceeding through an open transition state since stereocon-trol of the enolate geometry was not possible. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:4782 / 4784
页数:3
相关论文
共 51 条
[41]   STEREOSELECTIVE SYNTHESIS OF BETA-FLUOROALLYL ALCOHOLS [J].
TAGUCHI, T ;
TAKIGAWA, T ;
TAWARA, Y ;
MORIKAWA, T ;
KOBAYASHI, Y .
TETRAHEDRON LETTERS, 1984, 25 (49) :5689-5692
[42]   PREPARATION AND SOME REACTIONS OF TRIFLUOROVINYLLITHIUM [J].
TARRANT, P ;
SAVORY, J ;
JOHNCOCK, P .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (03) :839-&
[43]   DIASTEREOSELECTIVITY IN THE DIRECTED ALDOL REACTIONS OF 1-FLUORO-3,3-DIMETHYL-BUTANONE ENOLATES AND ENOL SILYL ETHERS [J].
WELCH, JT ;
SEPER, KW .
TETRAHEDRON LETTERS, 1984, 25 (46) :5247-5250
[44]   IMPROVED PROCEDURE FOR INTRODUCING THE ALPHA-FLUOROACETYL GROUP VIA THE DIRECTED ALDOL REACTION [J].
WELCH, JT ;
ESWARAKRISHNAN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5403-5405
[45]   PREPARATION OF ALPHA-FLUORO ENOLATES AND THEIR USE IN THE DIRECTED ALDOL REACTION [J].
WELCH, JT ;
SEPER, K ;
ESWARAKRISHNAN, S ;
SAMARTINO, J .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (24) :4720-4721
[46]   ADVANCES IN THE PREPARATION OF BIOLOGICALLY-ACTIVE ORGANOFLUORINE COMPOUNDS [J].
WELCH, JT .
TETRAHEDRON, 1987, 43 (14) :3123-3197
[47]   A SHORT SYNTHESIS OF 2-DEOXY-2-FLUORO-RIBO-D-PENTOPYRANOSE [J].
WELCH, JT ;
ESWARAKRISHNAN, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (04) :186-188
[48]   THE STEREOSELECTIVE ALDOL CONDENSATION OF ALPHA-FLUOROACETATES [J].
WELCH, JT ;
PLUMMER, JS .
SYNTHETIC COMMUNICATIONS, 1989, 19 (5-6) :1081-1090
[49]   FACILE DIASTEREOSELECTIVE ESTER ENOLATE CLAISEN REARRANGEMENTS OF ALLYL FLUOROACETATES [J].
WELCH, JT ;
SAMARTINO, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (19) :3663-3665
[50]  
WELCH JT, UNPUB STRUCTURAL CHE