Stereoselective, nonracemic synthesis of ω-borono-α-amino acids

被引:73
作者
Collet, S [1 ]
Bauchat, P [1 ]
Danion-Bougot, R [1 ]
Danion, D [1 ]
机构
[1] Univ Rennes 1, UMR 6510, F-35042 Rennes, France
关键词
D O I
10.1016/S0957-4166(98)00186-4
中图分类号
O61 [无机化学];
学科分类号
070301 [无机化学]; 081704 [应用化学];
摘要
omega-Unsaturated alpha-amino acids are synthesized through condensation of allyl and propargyl bromides or of 9-bromoundecene with a Ni(II) complex of the Schiff base derived from glycine and BPB. Hydroboration with Ipc(2)BH followed by oxidation with acetaldehyde affords enantiomerically pure omega-borono-alpha-aminocarboxylic acids. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2121 / 2131
页数:11
相关论文
共 23 条
[1]
*ACROS ORG, 275412500 ACROS ORG
[2]
Inhibition of Mn-2(2+)-arginase by borate leads to the design of a transition state analogue inhibitor, 2(S)-amino-6-boronohexanoic acid [J].
Baggio, R ;
Elbaum, D ;
Kanyo, ZF ;
Carroll, PJ ;
Cavalli, RC ;
Ash, DE ;
Christianson, DW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (34) :8107-8108
[3]
Belokon Y.N., 1988, IAN SSSR KH
[4]
GENERAL-METHOD OF DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF BETA-HYDROXY-ALPHA-AMINO ACIDS BY CONDENSATION OF ALDEHYDES AND KETONES WITH GLYCINE [J].
BELOKON, YN ;
BULYCHEV, AG ;
VITT, SV ;
STRUCHKOV, YT ;
BATSANOV, AS ;
TIMOFEEVA, TV ;
TSYRYAPKIN, VA ;
RYZHOV, MG ;
LYSOVA, LA ;
BAKHMUTOV, VI ;
BELIKOV, VM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (14) :4252-4259
[5]
ASYMMETRIC-SYNTHESIS OF S-5-BENZYLOXYTRYPTOPHAN, S-ALPHA-ALLYLGLYCINE AND S-BETA-(2-NAPHTHYL)ALANINE [J].
BELOKON, YN ;
CHERNOGLAZOVA, NI ;
IVANOVA, EV ;
POPKOV, AN ;
SAPOROVSKAYA, MB ;
SUVOROV, NN ;
BELIKOV, VM .
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1988, 37 (12) :2541-2544
[6]
BELOKON YN, 1992, JANSSEN CHIM ACTA, V10, P4
[7]
DIRECT CHIRAL SYNTHESIS OF BORONIC ACIDS AND ESTERS OF HIGH OPTICAL PURITY VIA ASYMMETRIC HYDROBORATION DISPLACEMENT [J].
BROWN, HC ;
JADHAV, PK ;
DESAI, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (15) :4303-4304
[8]
Hydroboration of vinylglycine and allylglycine as a route to boron-derivatives of alpha-amino acids. [J].
Denniel, V ;
Bauchat, P ;
Danion, D ;
DanionBougot, R .
TETRAHEDRON LETTERS, 1996, 37 (29) :5111-5114
[9]
SYNTHESIS OF [4-CARBORANYLALANINE, 5-LEUCINE]-ENKEPHALIN - (INCLUDING AN IMPROVED PREPARATION OF TERT-BUTOXYCARBONYL-L-ORTHO-CARBORANYLALANINE, NEW DERIVATIVES OF L-PROPARGYLGLYCINE, AND A NOTE ON MELANOTROPIC AND OPIATE RECEPTOR-BINDING CHARACTERISTICS) [J].
FAUCHERE, JL ;
LEUKART, O ;
EBERLE, A ;
SCHWYZER, R .
HELVETICA CHIMICA ACTA, 1979, 62 (05) :1385-1395
[10]
NOTE ON ISOLATION OF 2-OXAZOLINONE AND OXAZOLIUM-5-OLATE FORMS OF 2,4-DIARYLOXAZOLIN-5-ONES [J].
HOFLE, G ;
STEGLICH, W ;
DANIEL, H .
CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (07) :2648-2650