One-pot synthesis of trisubstituted 1,2-amino alcohols from deprotonated α-amino nitriles

被引:10
作者
Kison, Coralie [2 ]
Opatz, Till [1 ]
机构
[1] Univ Hamburg, Inst Organ Chem, D-20146 Hamburg, Germany
[2] Johannes Gutenberg Univ Mainz, Inst Organ Chem, D-55128 Mainz, Germany
关键词
amino alcohols; umpolung; amino nitriles; reduction;
D O I
10.1002/ejoc.200701205
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short synthesis of N,1,2-trisubstituted vicinal amino alcohols by 1,2-addition of deprotonated N-monosubstituted a-amino nitrites to aldehydes and subsequent one-pot reduction of the intermediates with borane-THF is described. This procedure leads to the predominant formation of the anti-configured products. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
引用
收藏
页码:2740 / 2745
页数:6
相关论文
共 31 条
[1]   AN IMPROVED, CONVENIENT PROCEDURE FOR REDUCTION OF AMINO-ACIDS TO AMINOALCOHOLS - USE OF NABH4-H2SO4 [J].
ABIKO, A ;
MASAMUNE, S .
TETRAHEDRON LETTERS, 1992, 33 (38) :5517-5518
[2]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[3]   Synthesis of γ-amino acid esters by 1,4-addition of deprotonated α-aminonitriles and α-(alkylideneamino)nitriles to α,β-unsaturated esters [J].
Bergner, Ines ;
Opatz, Till .
SYNTHESIS-STUTTGART, 2007, (06) :918-928
[4]   CHIRAL SYNTHESIS VIA ORGANOBORANES .14. SELECTIVE REDUCTIONS .41. DIISOPINOCAMPHEYLCHLOROBORANE, AN EXCEPTIONALLY EFFICIENT CHIRAL REDUCING AGENT [J].
BROWN, HC ;
CHANDRASEKHARAN, J ;
RAMACHANDRAN, PV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1539-1546
[5]   N-METALLO-IMINES - A NEW APPROACH TO ALPHA-AMINO ALCOHOLS FROM CYANOHYDRINS [J].
CAINELLI, G ;
MEZZINA, E ;
PANUNZIO, M .
TETRAHEDRON LETTERS, 1990, 31 (24) :3481-3484
[6]   SILYL NITRONATES - IMPROVED NITRO-ALDOL REACTIONS AND REDUCTIVE ROUTES TO 2-AMINOALCOHOLS [J].
COLVIN, EW ;
SEEBACH, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (16) :689-691
[7]   IMPROVED NITROALDOL REACTIONS AND REDUCTIVE ROUTES TO VICINAL AMINOALCOHOLS [J].
COLVIN, EW ;
BECK, AK ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1981, 64 (07) :2264-2271
[8]   HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].
COREY, EJ ;
BAKSHI, RK ;
SHIBATA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553
[9]   Some recent applications of α-amino nitrile chemistry [J].
Enders, D ;
Shilvock, JP .
CHEMICAL SOCIETY REVIEWS, 2000, 29 (05) :359-373
[10]   Diastereoselective reduction of α-aminoketones:: Synthesis of anti- and syn-β-aminoalcohols [J].
Fraser, DS ;
Park, SB ;
Chong, JM .
CANADIAN JOURNAL OF CHEMISTRY, 2004, 82 (02) :87-101