Magnesium bis(diisopropylamide), a useful reagent for regio- and stereoselective synthesis of kinetic silyl enol ethers

被引：23

作者：

Lessène, G ^{[1
]}

Tripoli, R ^{[1
]}

Cazeau, P ^{[1
]}

Biran, C ^{[1
]}

Bordeau, M ^{[1
]}

机构：

[1] Univ Bordeaux 1, Chim Organ & Organomet Lab, CNRS, UMR 5802, F-33405 Talence, France

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 21期

关键词：

D O I：

10.1016/S0040-4039(99)00665-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Less highly substituted silyl enol ethers are regiospecifically prepared in high yield, around room temperature under kinetic conditions, from unsymmetrical cyclic ketones and magnesium bis(diisopropylamide) [(DA)(2)Mg] in THF/heptane. This high regioselectivity is markedly higher than these reported for bromomagnesium diisopropylamide (DAMgBr); it is also similar to this of LDA/DME at -78 degrees C, but (DA)(2)Mg can be used at room temperature. In addition, a high E-enolization stereoselectivity is observed for benzylic ketones, reverse of this obtained with LDA. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：4037 / 4040

页数：4

共 24 条

[1] STEREOSELECTIVE ELECTROCHEMICAL SYNTHESIS OF SILYL ENOL ETHERS USING A SACRIFICIAL MAGNESIUM ANODE
BONAFOUX, D
BORDEAU, M
BIRAN, C
DUNOGUES, J
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 493 (1-2) : 27 - 32
[2] Regio- and stereoselective synthesis of silyl enol ethers using a new base electrogenerated from hexamethyldisilazane
Bonafoux, D
Bordeau, M
Biran, C
Cazeau, P
Dunogues, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) : 5532 - 5536
[3] Solid state structures and dynamic solution equilibria of bis(dibenzylamido)magnesium complexes: Aggregation dependence on stoichiometry and denticity of donor solvent
Clegg, W
Craig, FJ
Henderson, KW
Kennedy, AR
Mulvey, RE
O'Neil, PA
Reed, D
[J]. INORGANIC CHEMISTRY, 1997, 36 (27) : 6238 - 6246
[4] HIGHLY SELECTIVE, KINETICALLY CONTROLLED ENOLATE FORMATION USING LITHIUM DIALKYLAMIDES IN THE PRESENCE OF TRIMETHYLCHLOROSILANE
COREY, EJ
GROSS, AW
[J]. TETRAHEDRON LETTERS, 1984, 25 (05) : 495 - 498
[5] CHEMISTRY OF OXAZIRIDINES .14. ASYMMETRIC OXIDATION OF KETONE ENOLATES USING ENANTIOMERICALLY PURE (CAMPHORYLSULFONYL)OXAZIRIDINE
DAVIS, FA
SHEPPARD, AC
CHEN, BC
HAQUE, MS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (18) : 6679 - 6690
[6] MAGNESIUM AMIDE BASES AND AMIDO-GRIGNARDS .1. ORTHO-MAGNESIATION
EATON, PE
LEE, CH
XIONG, YH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) : 8016 - 8018
[7] HIGHLY HINDERED AMIDO-LITHIUM AND AMIDO-MAGNESIUM COMPLEXES - CRYSTAL-STRUCTURES OF [LI(MU-N(SIME3)2)(TETRAHYDROFURAN)]2 AND [MGBUS(MU-N(SIME3)2)]2
ENGELHARDT, LM
JOLLY, BS
JUNK, PC
RASTON, CL
SKELTON, BW
WHITE, AH
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1986, 39 (09) : 1337 - 1345
[8] CONDENSATION OF CERTAIN ESTERS BY MEANS OF DIETHYLAMINOMAGNESIUM BROMIDE
HAUSER, CR
WALKER, HG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (02) : 295 - 297
[9] ACYCLIC STEREOSELECTION .35. EFFECT OF CATION ON DIASTEREOFACIAL SELECTIVITY IN ALDOL REACTIONS OF A CHIRAL ALPHA-SILYLOXY KETONE
HEATHCOCK, CH
ARSENIYADIS, S
[J]. TETRAHEDRON LETTERS, 1985, 26 (49) : 6009 - 6012
[10] ACYCLIC STEREOSELECTION .7. STEREOSELECTIVE SYNTHESIS OF 2-ALKYL-3-HYDROXY CARBONYL-COMPOUNDS BY ALDOL CONDENSATION
HEATHCOCK, CH
BUSE, CT
KLESCHICK, WA
PIRRUNG, MC
SOHN, JE
LAMPE, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (06) : 1066 - 1081

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