Kinetic resolution of alcohols using a 1,2-dihydroimidazo[1,2-a]quinoline enantioselective acylation catalyst

被引：102

作者：

Birman, VB ^{[1
]}

Jiang, H ^{[1
]}

机构：

[1] Washington Univ, Dept Chem, St Louis, MO 63130 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 16期

关键词：

D O I：

10.1021/ol051063v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new enantioselective acylation catalyst (CI-PIO), designed to provide enhanced T-stacking with benzylic and cinnamyl alcohol substrates, was found to give considerably increased reaction rates and selectivities compared with the first-generation catalyst CF3-PIP.

引用

页码：3445 / 3447

页数：3

共 32 条

[1] The kinetic resolution of allylic alcohols by a non-enzymatic acylation catalyst; application to natural product synthesis
Bellemin-Laponnaz, S
Tweddell, J
Ruble, JC
Breitling, FM
Fu, GC
[J]. CHEMICAL COMMUNICATIONS, 2000, (12) : 1009 - 1010
[2] 2,3-dihydroimidazo[1,2-a]pyridines: A new class of enantioselective acyl transfer catalysts and their use in kinetic resolution of alcohols
Birman, VB
Uffman, EW
Hui, J
Li, XM
Kilbane, CJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (39) : 12226 - 12227
[3] BIRMAN VB, 2005, 229 NAT M AM CHEM SO
[4] BIRMAN VB, 2005, TETRAHEDRON
[5] POLYCYCLIC FUSED AMIDINES .3. AN UNEXPECTED MODE OF CYCLIZATION OF 2-PHENACYLISOQUINOLINIUM BROMIDE
COOKSON, RF
NOWOTNIK, DP
PARFITT, RT
AIREY, JE
KENDE, AS
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (02): : 201 - 204
[6] Kinetic resolution of sec-alcohols using a new class of readily assembled (S)-proline-derived 4-(pyrrolidino)-pyridine analogues
Dalaigh, CO
Hynes, SJ
Maher, DJ
Connon, SJ
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (06) : 981 - 984
[7] In the golden age of organocatalysis
Dalko, PI
Moisan, L
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) : 5138 - 5175
[8] Nucleophilic chiral amines as catalysts in asymmetric synthesis
France, S
Guerin, DJ
Miller, SJ
Lectka, T
[J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2985 - 3012
[9] Asymmetric catalysis with "planar-chiral" derivatives of 4-(dimethylamino)pyridine
Fu, GC
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) : 542 - 547
[10] CYCLIC AMIDINES .25. DERIVATIVES OF 1-ALKYL-2-AMINOQUINOLIN-4(1H)-ONES AND 2,3-DIHYDROIMIDAZO[1,2-A]QUINOLIN-5(1H)-ONE
GROUT, RJ
HYNAM, BM
PARTRIDGE, MW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (12): : 1314 - 1320

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