Asymmetric synthesis of α,α-disubstituted α-amino acid derivatives using MABR promoted rearrangement

被引:26
作者
Matsushita, M [1 ]
Maeda, H [1 ]
Kodama, M [1 ]
机构
[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Yamashiro, Tokushima 7708514, Japan
关键词
D O I
10.1016/S0040-4039(98)00576-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient route for the asymmetric synthesis of alpha,alpha-disubstituted alpha-amino acids derivatives (1, 2, and 3) starting from readily available epoxy silyl ethers (6) has been developed. High enantiomeric purity can be realized by the present method using a combination of MABR rearrangement of a chiral epoxide and Curtius rearrangement. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3749 / 3752
页数:4
相关论文
共 22 条
[1]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938
[2]   TOTAL SYNTHESIS OF (+)-LACTACYSTIN FROM D-GLUCOSE [J].
CHIDA, N ;
TAKEOKA, J ;
TSUTSUMI, N ;
OGAWA, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (07) :793-794
[3]  
CHIDA N, 1996, 38 S CHEM NAT PROD S, P259
[4]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[5]   Et(2)AlCl-catalyzed cyclization of epoxytrichloroacetimidates for the synthesis of alpha-substituted serines [J].
Hatakeyama, S ;
Matsumoto, H ;
Fukuyama, H ;
Mukugi, Y ;
Irie, H .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :2275-2279
[6]  
Hunt S., 1985, Chemistry and Biochemistry of the Amino Acids, P55, DOI DOI 10.1007/978-94-009-4832-7_4
[7]   Stereocontrolled synthesis of alpha,alpha-disubstituted alpha-aminoaldehydes and alpha-aminoacids using a [3,3] allylic trichloracetimidate rearrangement [J].
Imogai, H ;
Petit, Y ;
Larcheveque, M .
TETRAHEDRON LETTERS, 1996, 37 (15) :2573-2576
[8]   AN IMPROVED PROCEDURE FOR THE PREPARATION OF THE DESS-MARTIN PERIODINANE [J].
IRELAND, RE ;
LIU, LB .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) :2899-2899
[9]   LEWIS ACID-CATALYZED PREPARATION OF SOME CARBAMATES AND SULFONYLUREAS - APPLICATION TO THE DETERMINATION OF ENANTIOMERIC PURITY OF CHIRAL ALCOHOLS [J].
IRIE, H ;
NISHIMURA, M ;
YOSHIDA, M ;
IBUKA, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (07) :1209-1210
[10]   THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].
KATSUKI, T ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976