Anionic versus photochemical diastereoselective deconjugation of diacetone D-glucose α,β-unsaturated esters

被引：16

作者：

Bargiggia, F ^{[1
]}

Piva, O ^{[1
]}

机构：

[1] Univ Lyon 1, UMR CNRS 5622, Lab Chim Organ Photochim & Synth, F-69622 Villeurbanne, France

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 13期

关键词：

D O I：

10.1016/S0957-4166(03)00365-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Deconjugation of diacetone D-glucose alpha, beta-unsaturated esters has been conducted by deprotonation using NaHMDS with HMPA as co-solvent followed by stereoselective protonation at low temperature. High selectivities (>95%) were obtained with oc-methyl linear compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：1819 / 1827

页数：9

共 40 条

[11] Major sex pheromone component of female herald moth Scoliopteryx libatrix is the novel branched alkene (6Z, 13)-methylheneicosene [J].

Francke, W ;

Plass, E ;

Zimmermann, N ;

Tietgen, H ;

Tolasch, T ;

Franke, S ;

Subchev, M ;

Toshova, T ;

Pickett, JA ;

Wadhams, LJ ;

Woodcock, CM .

JOURNAL OF CHEMICAL ECOLOGY, 2000, 26 (05) :1135-1149

[12] BINAPHTHOL AS A CHIRAL AUXILIARY - DIASTEREOSELECTIVE ALKYLATION OF BINAPHTHYL ESTERS OF ALPHA,BETA-UNSATURATED CARBOXYLIC-ACIDS [J].

FUJI, K ;

TANAKA, F ;

NODE, M .

TETRAHEDRON LETTERS, 1991, 32 (49) :7281-7282

[13] Stereochemical consequences in the deprotonation of enoates [J].

Galatsis, P ;

Manwell, JJ ;

Millan, SD .

TETRAHEDRON LETTERS, 1996, 37 (30) :5261-5264

[14]

HARRIS FL, 1984, TETRAHEDRON LETT, V25, P1333

[15]

HEATHCOCK CH, 1992, TOPICS CARBANIONS CH, P1

[16] Asymmetric photodeconjugation of ammonium ene-carboxylates:: temperature effects and evidence for the α-carbon of the dienolic species as a latent trigonal centre [J].

Hénin, F ;

Létinois, S ;

Muzart, J .

TETRAHEDRON-ASYMMETRY, 2000, 11 (09) :2037-2044

[17]

HOGBERG HE, 1992, J ORG CHEM, V57, P2052

[18] MENTHYL 2-BROMOCROTONATE AND MENTHYL 4-BROMOCROTONATE - REAGENTS FOR CHIRAL VINYLOGOUS DARZEN AND REFORMATSKY REACTIONS [J].

HUDLICKY, T ;

RADESCA, L ;

RIGBY, HL .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) :4397-4399

[19] DECONJUGATION OF ALPHA,BETA-UNSATURATED ESTERS AND AN INTRAMOLECULAR MICHAEL REACTION OF BIS-ALPHA,BETA-UNSATURATED ESTERS WITH TRIALKYLSILYL TRIFLUOROMETHANESULFONATE IN THE PRESENCE OF TERTIARY AMINE - SYNTHESIS OF (PLUS-OR-MINUS)-RICCIOCARPIN-A [J].

IHARA, M ;

SUZUKI, S ;

TANIGUCHI, N ;

FUKUMOTO, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (19) :2251-2258

[20] A PRACTICAL SYNTHESIS OF (Z)-3-ALKENOATES [J].

IKEDA, Y ;

YAMAMOTO, H .

TETRAHEDRON LETTERS, 1984, 25 (45) :5181-5182

← 1 2 3 4 →