High stereocontrol in the allylation of chiral non-racemic α-alkoxy and α-amino nitrones

被引：24

作者：

Merino, P ^{[1
]}

Delso, I ^{[1
]}

Mannucci, V ^{[1
]}

Tejero, T ^{[1
]}

机构：

[1] Univ Zaragoza, Fac Ciencias, Inst Ciencia Mat Aragon, Dept Quim Organ,Lab Sintesis Asimetr, E-50009 Zaragoza, Spain

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 19期

关键词：

D O I：

10.1016/j.tetlet.2006.03.004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereocontrolled addition of allylic metals to chiral non-racemic nitrones promoted by the addition of Lewis acids is described. Whereas for alpha-alkoxy nitrones the stereocontrol depends on the Lewis acid used as an activator, for alpha-amino nitrones the diastercofacial course of the reaction depends on the protection of the a-amino group. The successful implementation of the methodology is represented by the enantiodivergent synthesis of D- and L-allylglycine. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3311 / 3314

页数：4

共 50 条

[1] Nucleophilic additions of chiral non-racemic enolates to N-benzyl-C-(alkoxymethyl) nitrones
Merino, P
Franco, S
Mates, JA
Merchan, FL
Romero, P
Tejero, T
Uriel, S
Matute, R
[J]. ARKIVOC, 2004, : 48 - 58
[2] A route to chiral, non-racemic macroheterocycles
Hughes, R
Meyers, AI
[J]. TETRAHEDRON, 1998, 54 (33) : 9895 - 9902
[3] Epimerization of non-racemic chiral zirconocenes
Buck, Richard M.
Jordan, Richard F.
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 350 - 350
[4] SYNTHESIS AND THERMOLYSIS OF A CHIRAL, NON-RACEMIC IMINOAZIRIDINE
QUAST, H
ALDENKORTT, S
HELLER, E
SCHAFER, P
SCHMITT, E
[J]. CHEMISCHE BERICHTE, 1994, 127 (09) : 1699 - 1706
[5] Experimental and theoretical studies on Mannich-type reactions of chiral non-racemic N-(benzyloxyethyl) nitrones
Diez-Martinez, Alba
Tejero, Tomas
Merino, Pedro
[J]. TETRAHEDRON-ASYMMETRY, 2010, 21 (24) : 2934 - 2943
[6] Synthesis of chiral non-racemic substituted vinyl aziridines
Chigboh, Kordi
Morton, Daniel
Nadin, Alan
Stockman, Robert A.
[J]. TETRAHEDRON LETTERS, 2008, 49 (32) : 4768 - 4770
[7] ASYMMETRIC SYNTHESES FROM CHIRAL NON-RACEMIC OXAZOLINES
MEYERS, AL
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1974, : 34 - 34
[8] ω-Transaminases for the synthesis of non-racemic α-chiral primary amines
Koszelewski, Dominik
Tauber, Katharina
Faber, Kurt
Kroutil, Wolfgang
[J]. TRENDS IN BIOTECHNOLOGY, 2010, 28 (06) : 324 - 332
[9] Straightforward synthesis of chiral non-racemic α-boryl isocyanides
Fini, Francesco
Zanni, Alessandro
Introvigne, Maria Luisa
Stucchi, Mattia
Caselli, Emilia
Prati, Fabio
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (30) : 6687 - 6691
[10] Diastereoselective cycloadditions of chiral non-racemic azomethine imines
Roussi, F
Chauveau, A
Bonin, M
Micouin, L
Husson, HP
[J]. SYNTHESIS-STUTTGART, 2000, (08): : 1170 - 1179

← 1 2 3 4 5 →