Diastereoselective Michael addition of (S)-mandelic acid enolate to nitroalkenes.: Enantioselective synthesis of α-hydroxy-α,β-diaryl-γ-lactams

被引：19

作者：

Blay, G ^{[1
]}

Fernández, I ^{[1
]}

Monje, B ^{[1
]}

Pedro, JR ^{[1
]}

机构：

[1] Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Valencia, Spain

来源：

TETRAHEDRON | 2004年 / 60卷 / 01期

关键词：

nitrostyrenes; 1,4-addition; dioxolanone; GABA; self-regeneration of stereocenters;

D O I：

10.1016/j.tet.2003.10.081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of the lithium enolate of the (S,S)-cis-1,3-dioxolan-4-one derived from optically active (S)-mandelic acid and pivalaldehyde with several aromatic nitroalkenes in the presence of HMPA proceeds readily to give the corresponding Michael adducts in good yields and diastereoselectivities. Reduction of the nitro group with Zn/HCl/EtOH/H2O with concomitant intramolecular aminolysis of the acetal moiety leads directly to enantiomerically pure alpha-hydroxy-alpha,beta-diaryl-gamma-lactams. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：165 / 170

页数：6

共 41 条

[1] Flash vacuum pyrolysis of stabilised phosphorus ylides.: Part 17.: Preparation of aliphatic amino acid derived γ-alkoxycarbonyl-amino-β-oxo ylides and pyrolysis to give α,β-acetylenic γ-amino acid and GABA analogues
Aitken, RA
Karodia, N
Massil, T
Young, RJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (04): : 533 - 541
[2] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene
Alexakis, A
Andrey, O
[J]. ORGANIC LETTERS, 2002, 4 (21) : 3611 - 3614
[3] Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221
[4] An asymmetric synthesis of the novel H3 agonist (+)-(3R,4R)-3-(4-imidazolyl)-4-methylpyrrolidine dihydrochloride (Sch 50971)
Aslanian, R
Lee, G
Iyer, RV
Shih, NY
Piwinski, JJ
Draper, RW
McPhail, AT
[J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (19) : 3867 - 3871
[5] Enantioselective synthesis of 2-substituted 4-aminobutanoic acid (GABA) analogues via cyanomethylation of chiral enolates
Azam, S
DSouza, AA
Wyatt, PB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (07): : 621 - 627
[6] Baxendale IR, 2002, SYNLETT, P1641
[7] Highly diastereoselective Michael reaction of (S)-mandelic acid enolate.: Chiral benzoyl carbanion equivalent through an oxidative decarboxylation of α-hydroxyacids
Blay, G
Fernández, I
Monje, B
Pedro, JR
Ruiz, R
[J]. TETRAHEDRON LETTERS, 2002, 43 (47) : 8463 - 8466
[8] Brenner M, 1999, HELV CHIM ACTA, V82, P2365, DOI 10.1002/(SICI)1522-2675(19991215)82:12<2365::AID-HLCA2365>3.0.CO
[9] 2-#
[10] ASYMMETRIC MICHAEL-ADDITIONS - STEREOSELECTIVE ALKYLATION OF CHIRAL, NON-RACEMIC ENOLATES BY NITROOLEFINS - PREPARATION OF ENANTIOMERICALLY PURE GAMMA-AMINOBUTYRIC AND SUCCINIC ACID-DERIVATIVES
CALDERARI, G
SEEBACH, D
[J]. HELVETICA CHIMICA ACTA, 1985, 68 (06) : 1592 - 1604

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