Stereoselective formation of quaternary carbon centres with chiral 3-sulfonyl-1,3-oxazolidines and titanium enolates

被引：3

作者：

Brüggemann, M ^{[1
]}

Fröhlich, R ^{[1
]}

Wibbeling, B ^{[1
]}

Holst, C ^{[1
]}

Hoppe, D ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

TETRAHEDRON | 2002年 / 58卷 / 02期

关键词：

oxazolidines; enolates; titanium and compounds; asymmetric reactions;

D O I：

10.1016/S0040-4020(01)01150-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of chiral 2-alkoxy-3-sulfonyl-1,3-oxazolidines and trichlorotitanium enolates was applied for the stereoselective construction of quaternary a-carbonyl stereocentres on cycloalkanones. The influence of different chiral 1,3-oxazolidines on the selectivity and yield of this reaction has been studied. 2-Alkoxy-3-sulfonyl-1,3-oxazolidines bearing one small group in the 4 position or two trans-arranged groups in the 4 and 5 position have been found to give the best results. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：321 / 340

页数：20

共 22 条

[21] The chemistry of metallacyclic alkenylcarbene complexes .3. C-C bond formation with carbon nucleophiles. Stereoselective dienylation of lithium enolates and cuprates and a novel cascade synthesis of highly substituted cyclopentenones from lithium acetylides
Bohmer, J
Fortsch, W
Hampel, F
Schobert, R
[J]. CHEMISCHE BERICHTE, 1996, 129 (04) : 427 - 433
[22] Completely stereoselective P-C bond formation via base-induced [1,3]- and [1,2]-intramolecular rearrangements of aryl phosphinates, phosphinoamidates and related compounds:: generation of P-chiral β-hydroxy, β-mercapto- and α-amino tertiary phosphine oxides and phosphine sulfides
Au-Yeung, TL
Chan, KY
Haynes, RK
Williams, ID
Yeung, LL
[J]. TETRAHEDRON LETTERS, 2001, 42 (03) : 457 - 460

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