Non-enzymatic kinetic resolution of 1,2-azidoalcohols using a planar-chiral DMAP derivative catalyst

被引：11

作者：

Mesas-Sanchez, Laura ^{[1
]}

Diaz-Alvarez, Alba E. ^{[1
]}

Diner, Peter ^{[1
]}

机构：

[1] Uppsala Univ, Dept Chem BMC, SE-75123 Uppsala, Sweden

来源：

TETRAHEDRON | 2013年 / 69卷 / 02期

关键词：

Non-enzymatic kinetic resolution; 1,2-Azidoalcohols; Planar-chiral DMAP derivative catalyst; Ferrocenyl catalyst; ENANTIOSELECTIVE ACYL TRANSFER; CHEMOENZYMATIC SYNTHESIS; ASYMMETRIC CATALYSIS; PYRIDINE CATALYSTS; SECONDARY ALCOHOLS; BETA-AZIDOALCOHOLS; SEC-ALCOHOLS; ACYLATION; 4-PYRROLIDINOPYRIDINE; AZIRIDINES;

D O I：

10.1016/j.tet.2012.10.077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically pure 1,2-azidoalcohols are widely used as precursors for other high value organic products. A non-enzymatic kinetic resolution procedure for the stereoselective synthesis of chiral 1,2-azidoalcohols from the readily available racemic counterparts has been developed, employing a planar-chiral DMAP derivative catalyst. Following this procedure, a range of aromatic 1,2-azidoalcohols was obtained in good selectivities (up to S=45) and high enantiomeric excess (up to 99% ee). (c) 2012 Elsevier Ltd. All rights reserved.

引用

页码：753 / 757

页数：5

共 32 条

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Diaz-Alvarez, Alba E.
Mesas-Sanchez, Laura
Diner, Peter
MOLECULES, 2014, 19 (09): : 14273 - 14291
[2] Nonenzymatic kinetic resolution of propargylic alcohols by a planar-chiral DMAP derivative: Crystallographic characterization of the acylated catalyst
J Am Chem Soc, 21 (5091):
[3] Nonenzymatic kinetic resolution of propargylic alcohols by a planar-chiral DMAP derivative: Crystallographic characterization of the acylated catalyst
Tao, Beata
Ruble, J. Craig
Hoic, Diego A.
Fu, Gregory C.
Journal of the American Chemical Society, 1999, 121 (44):
[4] Nonenzymatic kinetic resolution of propargylic alcohols by a planar-chiral DMAP derivative: Crystallographic characterization of the acylated catalyst
Tao, BT
Ruble, JC
Hoic, DA
Fu, GC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) : 5091 - 5092
[5] Kinetic resolution of arylalkylcarbinols catalyzed by a planar-chiral derivative of DMAP: A new benchmark for nonenzymatic acylation
Ruble, JC
Tweddell, J
Fu, GC
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09): : 2794 - 2795
[6] Asymmetric dihydroxylation of 2-substituted 1-vinylferrocenes:: The first non-enzymatic kinetic resolution of planar-chiral ferrocenes
Bueno, Agusti
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ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (18) : 2590 - 2596
[7] Nonenzymatic dynamic kinetic resolution of alcohols catalyzed by planar-chiral DMAP derivatives
Lee, Sarah Y.
Murphy, Jaclyn M.
Fu, Gregory C.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[8] Nonenzymatic kinetic resolution of propargylic alcohols by a planar-chiral DMAP derivative: Crystallographic characterization of the acylated catalyst (vol 121, pg 5091, 1999)
Tao, B
Ruble, JC
Hoic, DA
Fu, GC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (44) : 10452 - 10452
[9] Practical Access to Planar Chiral 1,2-(α-Ketotetramethylene)-ferrocene by Non-Enzymatic Kinetic Resolution and Conclusive Confirmation of its Absolute Configuration
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Zhou, Gang
Hall, Thomas H.
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Chen, Weiping
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (16-17) : 3453 - 3457
[10] A new benchmark for the non-enzymatic enantioselective acylation of amines: use of a planar-chiral derivative of 4-pyrrolidinopyridine as the acylating agent
Ie, Y
Fu, GC
CHEMICAL COMMUNICATIONS, 2000, (02) : 119 - 120

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