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

[1] Diastereoselective synthesis of 2-aminoalkyl-3-sulfonyl-1,3-oxazolidines on solid support
Conde-Frieboes, K
Schjeltved, RK
Breinholt, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25): : 8952 - 8957
[2] NORPSEUDOEPHEDRINE-DERIVED 2-METHOXY-3-SULFONYL-1,3-OXAZOLIDINES - CHIRAL, HIGHLY DIASTEREOSELECTIVE FORMYL CATION EQUIVALENTS
CONDEFRIEBOES, K
HOPPE, D
[J]. TETRAHEDRON, 1992, 48 (29) : 6011 - 6020
[3] Stereoselective formation of quaternary carbon centers:: Alkylation of α,α-disubstituted amide enolates
Manthorpe, JM
Gleason, JL
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (13) : 2338 - 2341
[4] A new route to the asymmetric synthesis of (-)-malyngolide and (-)-epi-malyngolide using N-sulfonyl-1,3-oxazolidines as chiral auxiliaries
Winter, E
Hoppe, D
[J]. TETRAHEDRON, 1998, 54 (35) : 10329 - 10338
[5] Highly regio- and stereoselective iodocyclization of chiral 3-alkoxycarbonyl-4-propenyl-2,2-dimethy-1,3-oxazolidines:: a computational investigation
Jordá-Gregori, JM
González-Rosende, ME
Sepúlveda-Arques, J
Galeazzi, R
Orena, M
[J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (06) : 1135 - 1143
[6] A simple stereoselective synthesis of enantiopure 2-substituted pyrrolidines and piperidines from chiral (R)-phenylglycinol-derived bicyclic 1,3-oxazolidines
Andrés, JM
Herráiz-Sierra, I
Pedrosa, R
Pérez-Encabo, A
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (09) : 1719 - 1726
[7] ENANTIOSELECTIVE SYNTHESIS OF ALPHA-BRANCHED ALPHA-HYDROXY KETONES VIA CHIRAL N-SULFONYL-2-ALKYL-2-CYANO-1,3-OXAZOLIDINES
HARDER, T
LOHL, T
BOLTE, M
WAGNER, K
HOPPE, D
[J]. TETRAHEDRON LETTERS, 1994, 35 (40) : 7365 - 7368
[8] A practical chiral bicyclic thioglycolate lactam auxiliary for stereoselective quaternary carbon formation
Arpin, A
Manthorpe, JM
Gleason, JL
[J]. ORGANIC LETTERS, 2006, 8 (07) : 1359 - 1362
[9] Aryl radical cyclization of chiral 3-allyl-2-(2-bromophenyl)-1,3-oxazolidines with tributyltin hydride
Yamauchi, T
Sugiyama, J
Higashiyama, K
[J]. HETEROCYCLES, 2002, 58 : 431 - 447
[10] ASYMMETRIC ALDOL ADDITION-REACTIONS OF A CHIRAL 3-SULFONYL-1,3-OXAZOLIDINE-MASKED LITHIUM 2-FORMYLCYCLOHEXANONE ENOLATE
HOPPE, I
HOPPE, D
HERBSTIRMER, R
EGERT, E
[J]. TETRAHEDRON LETTERS, 1990, 31 (47) : 6859 - 6862

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