Simple and practical routes to enantiomerically pure 5-(trialkylsilyl)-2-cyclohexenones

被引：39

作者：

Sarakinos, G ^{[1
]}

Corey, EJ ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 05期

关键词：

D O I：

10.1021/ol990805f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Enantiomerically pure chiral 5-silylated 2-cyclohexenones are easily prepared in high yield using as a key step kinetic resolution with a commercially available lipase. Fully active enzyme can be recovered very efficiently for reuse. The synthetic steps are outlined in Schemes 1 and 3. Enantiomerically pure 2 cyclohexenones such as 1 and 2 are versatile intermediates for the synthesis of a multitude of chiral targets by means of a variety of diastereoselective reactions such as those illustrated in Scheme 2.

引用

页码：811 / 814

页数：4

共 50 条

[31] Synthesis of enantiomerically pure 2′,3′,5′-trideoxy-4′-[(diethoxyphosphoryl)difluoromethyl]thymidine analogues
Arnone, A
Bravo, P
Frigerio, M
Mele, A
Vergani, B
Viani, F
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (09) : 2149 - 2157
[32] SYNTHESIS OF ENANTIOMERICALLY PURE 5-(L-MENTHYLOXY)-3,4-DIBROMO-2(5H)-FURANONE AND ITS TANDEM ASYMMETRIC MICHAEL ADDITION-ELIMINATION REACTION
CHEN, QH
GENG, Z
HUANG, B
TETRAHEDRON-ASYMMETRY, 1995, 6 (02) : 401 - 404
[33] Synthesis of enantiomerically pure 5-(L-menthyloxy)-3,4-dibromo-2(5H)-furan one and its tandem asymmetric Michael addition-elimination reaction
Chen, Q.
Zhe, G.
Bin, H.
Tetrahedron: Asymmetry, 6 (02):
[34] PRACTICAL ENZYMATIC RESOLUTION OF CHIRAL AUXILIARIES - ENANTIOMERICALLY PURE TRANS-2-PHENYLCYCLOHEXANOL AND TRANS-2-(ALPHA-CUMYL)CYCLOHEXANOL
WHITESELL, JK
LAWRENCE, RM
CHIMIA, 1986, 40 (09) : 318 - 321
[35] Synthesis of enantiomerically pure monosubstituted 1,2 lambda(5)-oxaphospholanes. Synthesis of homoallylic alcohols
Okuma, K
Tanaka, Y
Hirabayashi, S
Shioji, K
Matsuyama, H
HETEROCYCLES, 1997, 45 (07) : 1385 - 1390
[36] A simple and practical approach to enantiomerically pure (S)-3-hydroxy-γ-butyrolactone:: synthesis of (R)-4-cyano-3-hydroxybutyric acid ethyl ester
Kumar, P
Deshmukh, AN
Upadhyay, RK
Gurjar, MK
TETRAHEDRON-ASYMMETRY, 2005, 16 (16) : 2717 - 2721
[37] USEFUL SYNTHETIC ROUTES TO PURE EXO-5-VINYL-2-NORBORNENE AND ENDO-5-VINYL-2-NORBORNENE
INOUE, Y
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (05) : 1954 - 1956
[38] AN IMPROVED, PRACTICAL SYNTHESIS OF 5-[H-2]-D-GLUCOSE
HARDICK, DJ
HUTCHINSON, DW
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (03) : 409 - 414
[39] LIPASE CATALYZED RESOLUTION OF 1-TERT-BUTYLTHIO-2-ALKANOLS - ENZYME MEDIATED ROUTES TO ENANTIOMERICALLY PURE 1,2-EPOXYALKANES AND 2-ALKANOLS
GOERGENS, U
SCHNEIDER, MP
TETRAHEDRON-ASYMMETRY, 1992, 3 (09) : 1149 - 1152
[40] Routes for the Synthesis of (2S)-2-Methyltetrahydropyran-4-one from Simple Optically Pure Building Blocks
Anderson, Kevin R.
Atkinson, Stephanie L. G.
Fujiwara, Takahiro
Giles, Melvyn E.
Matsumoto, Takaji
Merifield, Eric
Singleton, John T.
Saito, Takao
Sotoguchi, Tsukasa
Tornos, James A.
Way, Edward L.
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2010, 14 (01) : 58 - 71

← 1 2 3 4 5 →