Facile preparation and functionalization of chiral stabilized ylides from common chiral auxiliaries using triphenylphosphoranylideneketene (the bestmann ylide) and their use in Wittig reactions

被引：11

作者：

Boeckman, Robert K., Jr. ^{[1
]}

Song, Xinyi ^{[1
]}

Pero, Joseph E. ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 23期

关键词：

D O I：

10.1021/jo061732y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Camphor-derived lactams and other related chiral controllers have been found to react with the Bestmann ylide (triphenyl-phosphoranylideneketene) upon heating in toluene. The resulting parent ylides provide convenient access to a structurally diverse set of chiral stabilized ylides via functionalization. The utility of these chiral ylides for Wittig reactions has been briefly investigated and the effects of alpha-substitution noted.

引用

页码：8969 / 8972

页数：4

共 8 条

[1] WITTIG REACTIONS OF YLIDE ANIONS DERIVED FROM STABILIZED YLIDES
MCKENNA, EG
WALKER, BJ
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (09) : 568 - 569
[2] THE STEREOCHEMISTRY OF WITTIG REACTIONS OF YLIDE-ANIONS DERIVED FROM SEMI-STABILIZED PHOSPHONIUM YLIDES
MCKENNA, EG
WALKER, BJ
TETRAHEDRON LETTERS, 1988, 29 (04) : 485 - 488
[3] THE USE OF CHIRAL AUXILIARIES AND DIASTEREOMERIC GROUP SELECTIVE REACTIONS IN THE PREPARATION OF NEW ASYMMETRIC TRANSITION-METAL REAGENTS
HEPPERT, JA
AUBE, J
THOMASMILLER, ME
BOYLE, TJ
MILLIGAN, ML
DIETZ, SD
TAKUSAGAWA, F
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1989, 197 : 111 - INOR
[4] Asymmetric Wittig reactions of chiral arsonium ylides.: Part 3:: Reversal of stereochemistry caused by metal cation in enantioselective olefination of 4-substituted cyclohexanones using a C2-symmetric chiral arsine
Dai, WM
Wu, AX
Wu, HF
TETRAHEDRON-ASYMMETRY, 2002, 13 (20) : 2187 - 2191
[5] Chiral recognition:: Design and preparation of chiral stationary phases using selectors derived from Ugi multicomponent condensation reactions and a combinatorial approach
Brahmachary, E
Ling, FH
Svec, F
Fréchet, JMJ
JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (04): : 441 - 450
[6] STEREOCONTROLLED PREPARATION OF CHIRAL SECONDARY ALPHA-METHYLENE GAMMA-LACTAMS BY ADDITION OF ORGANOZINC REAGENTS DERIVED FROM 2-(BROMOMETHYL)ACRYLATES TO IMINES USING BETA-AMINOALCOHOLS AS CHIRAL AUXILIARIES
DEMBELE, YA
BELAUD, C
VILLIERAS, J
TETRAHEDRON-ASYMMETRY, 1992, 3 (04) : 511 - 514
[7] Asymmetric synthesis using a new chiral a-functionalized allylboronate derived from endo-2-phenyl-exo-2,3-bornanediol: preparation and reactions with aldehydes
Chataigner, I.
Lebreton, J.
Zammattio, F.
Villieras, J.
Tetrahedron Letters, 38 (21):
[8] Asymmetric synthesis using a new chiral beta-functionalized allylboronate derived from endo-2-phenyl-exo-2,3-bornanediol: Preparation and reactions with aldehydes.
Chataigner, I
Lebreton, J
Zammattio, F
Villieras, J
TETRAHEDRON LETTERS, 1997, 38 (21) : 3719 - 3722

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