UNUSUAL REACTIONS OF SECONDARY AMINO-ACIDS WITH TRIFLUOROACETIC-ANHYDRIDE - A NOVEL ACCESS TO ALPHA-TRIFLUOROMETHYLATED ACYLOINS

被引:22
作者
KAWASE, M
机构
[1] Faculty of Pharmaceutical Sciences, Josai University, Sakado-shi, Saitama, 350-02
关键词
D O I
10.1016/0040-4039(94)88187-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new fragmentation reaction of secondary alpha-amino acids with trifluoroacetic anhydride under Dakin-West reaction conditions proceeds through oxazolium salt intermediates followed by ring cleavage to form alpha-trifluoromethylated acyloins in good yields.
引用
收藏
页码:149 / 152
页数:4
相关论文
共 14 条
[1]   PREPARATION OF TRIFLUOROMETHYL KETONES AND RELATED FLUORINATED KETONES [J].
BEGUE, JP ;
BONNETDELPON, D .
TETRAHEDRON, 1991, 47 (20-21) :3207-3258
[2]   A VERSATILE SYNTHESIS OF AMINO TRIFLUOROMETHYL KETONES AND ALCOHOLS [J].
BEGUE, JP ;
BONNETDELPON, D ;
SDASSI, H .
TETRAHEDRON LETTERS, 1992, 33 (14) :1879-1882
[3]   AN EXPEDIENT ACCESS TO TRIFLUOROMETHYL KETONES FROM CARBOXYLIC-ACIDS [J].
BOIVIN, J ;
ELKAIM, L ;
ZARD, SZ .
TETRAHEDRON LETTERS, 1992, 33 (10) :1285-1288
[4]   THE DAKIN-WEST REACTION [J].
BUCHANAN, GL .
CHEMICAL SOCIETY REVIEWS, 1988, 17 (02) :91-109
[5]   A METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF PEPTIDYL TRIFLUOROMETHYL KETONES [J].
EDWARDS, PD .
TETRAHEDRON LETTERS, 1992, 33 (30) :4279-4282
[6]   RECENT TRENDS IN THE SYNTHESIS OF ORGANOFLUORINE COMPOUNDS [J].
FUCHIKAMI, T .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1984, 42 (09) :775-785
[7]   FORMATION AND STRUCTURE OF CERTAIN OXAZOLONIUM COMPOUNDS [J].
GRECO, CV ;
GRAY, RP ;
GROSSO, VG .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (12) :4101-&
[8]   A FACILE ONE-POT SYNTHESIS OF 5-TRIFLUOROMETHYLOXAZOLES AND 5-PERFLUOROALKYLOXAZOLES FROM N-ALKYL-N-ACYLAMINO ACIDS [J].
KAWASE, M .
HETEROCYCLES, 1993, 36 (11) :2441-2444
[9]   UNEXPECTED PRODUCT FROM THE DAKIN-WEST REACTION OF N-ACYLPROLINES USING TRIFLUOROACETIC-ANHYDRIDE - A NOVEL ACCESS TO 5-TRIFLUOROMETHYLOXAZOLES [J].
KAWASE, M ;
MIYAMAE, H ;
NARITA, M ;
KURIHARA, T .
TETRAHEDRON LETTERS, 1993, 34 (05) :859-862
[10]  
KOLB M, 1990, LIEBIGS ANN CHEM, P1