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

[1] Evaluation and Development of Practical Routes to an Enantiomerically Pure C2-Symmetric Diamine Building Block
Karlsson, Staffan
Lindberg, Jan
Sorensen, Henrik
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2013, 17 (12) : 1552 - 1560
[2] SYNTHESIS OF SOME 2-CYCLOHEXENONES AND 2-METHOXY-2-OXABICYCLO(2.2.2) OCTANO-5-ONES
APARICIO, FJL
BENITEZ, FZ
MENDOZA, PG
GONZALEZ, FS
ANALES DE QUIMICA SERIE C-QUIMICA ORGANICA Y BIOQUIMICA, 1984, 80 (03): : 295 - 300
[3] Practical synthesis of enantiomerically pure 2-(diphenylphosphanyl)ferrocene carboxylic acid
Breit, B
Breuninger, D
SYNTHESIS-STUTTGART, 2005, (16): : 2782 - 2786
[4] A practical preparation of enantiomerically pure (R)- and (S)-2-bromohexadecanoic acids
Guo, JS
Knapp, DW
Boegeman, S
TETRAHEDRON-ASYMMETRY, 2000, 11 (20) : 4105 - 4111
[5] A route to enantiomerically pure 5-(2′-hydroxyethyl)cyclopent-2-en-1-ol and its absolute configuration by Mosher esters
Chen, Hao
Nagabandi, Srinivas
Smith, Steven
Goodman, Jonathan M.
Plettner, Erika
TETRAHEDRON-ASYMMETRY, 2009, 20 (04) : 449 - 456
[6] Direct Synthesis of Highly Substituted 2-Cyclohexenones and Sterically Hindered Benzophenones Based on a [5C+1C] Annulation
Fu, Zhenqian
Wang, Mang
Dong, Ying
Liu, Jun
Liu, Qun
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16): : 6105 - 6110
[7] Enantiomerically pure 2,2-dibromocyclopropanecarboxylic acids, simple chiral building blocks
Baird, MS
Licence, P
Tverezovsky, VV
Bolesov, IG
Clegg, W
TETRAHEDRON, 1999, 55 (09) : 2773 - 2784
[8] Preparation of enantiomerically pure 5-palladatricyclo[4.1.0.0(2,4)]heptanes and conversion into enantiomerically pure complexes with helical chirality at palladium
Hashmi, ASK
Naumann, F
Probst, R
Bats, JW
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (1-2) : 104 - 106
[9] INTRAMOLECULAR PHOTOCHEMICAL [2+2]-CYCLOADDITIONS OF ENANTIOMERICALLY PURE 4,4-DISUBSTITUTED CYCLOHEXENONES - AN APPROACH TO THE TOTAL ASYMMETRIC-SYNTHESIS OF LINTENONE
RESEK, JE
MEYERS, AI
SYNLETT, 1995, (02) : 145 - 146
[10] Chemoenzymatic routes to enantiomerically pure 2-azatyrosine and 2-, 3-and 4-pyridylalanine derivatives
Moussa, Amer
Meffre, Patrick
Martinez, Jean
Rolland, Valerie
AMINO ACIDS, 2012, 42 (04) : 1339 - 1348

← 1 2 3 4 5 →