A route to enantiomerically pure 5-(2′-hydroxyethyl)cyclopent-2-en-1-ol and its absolute configuration by Mosher esters

被引：7

作者：

Chen, Hao ^{[1
]}

Nagabandi, Srinivas ^{[1
]}

Smith, Steven ^{[2
]}

Goodman, Jonathan M. ^{[2
]}

Plettner, Erika ^{[1
]}

机构：

[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada

[2] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

TETRAHEDRON-ASYMMETRY | 2009年 / 20卷 / 04期

基金：

加拿大自然科学与工程研究理事会;

关键词：

CATALYZED KINETIC RESOLUTION; CARBOCYCLIC NUCLEOSIDES; LIPASE; ALCOHOLS; HIV;

D O I：

10.1016/j.tetasy.2009.02.007

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The (+/-)-5-(2'-hydroxyethyl)cyclopent-2-en-1-ol 1 was prepared in a one-pot procedure, and was resolved using lipase AK and vinyl acetate with high ee. This provides a readily available chiral synthon for the synthesis of a wide variety of biologically interesting molecules. Further, the absolute configuration of diol 1 was confirmed directly by the Mosher ester method. (c) 2009 Elsevier Ltd. All rights reserved.

引用

页码：449 / 456

页数：8

共 48 条

[1] Lipase-catalyzed kinetic resolution of Z-configured homoallylic alcohols
Adam, W
Saha-Möller, CR
Schmid, KS
[J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (02) : 315 - 322
[2] Palladium-catalyzed substitution of unsaturated lactones. Application to the synthesis of carbocyclic polyoxins and nikkomycins
Aggarwal, VK
Monteiro, N
Tarver, GJ
Lindell, SD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (04) : 1192 - 1193
[3] Palladium-catalyzed synthesis of cis-2-[4-(9H-purin-9-yl)-2-cyclopenten-1-yl]ethanol analogues
Akella, LB
Vince, R
[J]. TETRAHEDRON, 1996, 52 (08) : 2789 - 2794
[4] ENANTIOSELECTIVE SYNTHESIS OF THE CARBOCYCLIC NUCLEOSIDES (-)-ARISTEROMYCIN AND (-)-NEPLANOCIN-A BY A CHEMICOENZYMATIC APPROACH
ARITA, M
ADACHI, K
ITO, Y
SAWAI, H
OHNO, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (12) : 4049 - 4055
[5] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
BECKE, AD
[J]. JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) : 5648 - 5652
[6] DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR
BECKE, AD
[J]. PHYSICAL REVIEW A, 1988, 38 (06): : 3098 - 3100
[7] Formal synthesis of (±)-mitsugashiwalactone and (±)-isodihydronepetalactone from norborn-5-en-2-one involving Shapiro reaction
Chang, MY
Chang, NC
[J]. JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1999, 46 (01) : 41 - 45
[8] Further model studies related to fredericamycin A: Analogues in which ring C is expanded to six atoms, and an examination of the diastereoselectivity of radical spirocyclization
Clive, DLJ
Kong, XL
Paul, CC
[J]. TETRAHEDRON, 1996, 52 (17) : 6085 - 6116
[9] USE OF RADICAL RING-OPENING FOR INTRODUCTION OF ALKYL AND SUBSTITUTED ALKYL-GROUPS WITH STEREOCHEMICAL CONTROL - A SYNTHETIC APPLICATION OF CYCLOPROPYLCARBINYL RADICALS
CLIVE, DLJ
DAIGNEAULT, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) : 3801 - 3814
[10] THE STRUCTURE OF THE (2R)-3,3,3-TRIFLUORO-2-METHOXY-2-PHENYLPROPIONIC ACID ESTER OF TRANS-4-TERT-BUTYLCYCLOHEXANOL
DOESBURG, HM
PETIT, GH
MERCKX, EM
[J]. ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1982, 38 (APR): : 1181 - 1185

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