Diastereoselective One-Pot Knoevenagel Condensation/Corey-Chaykovsky Cyclopropanation

被引：16

作者：

Clemens, Jeremy J. ^{[1
]}

Asgian, Juliana L. ^{[1
]}

Busch, Brett B. ^{[1
]}

Coon, Timothy ^{[1
]}

Ernst, Justin ^{[1
]}

Kaljevic, Leonard ^{[1
]}

Krenitsky, Paul J. ^{[1
]}

Neubert, Timothy D. ^{[1
]}

Schweiger, Edwin J. ^{[1
]}

Termin, Andreas ^{[1
]}

Stamos, Dean ^{[1
]}

机构：

[1] Vertex Pharmaceut, Dept Drug Innovat, San Diego, CA 92121 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 02期

关键词：

FERROELECTRIC LIQUID-CRYSTALS; STEREOSELECTIVE-SYNTHESIS; DILITHIATED NITRILES; CYANOCYCLOPROPANES; EPIBROMOHYDRIN; SELECTIVITY; CYCLIZATION; EPOXIDATION; DOPANTS;

D O I：

10.1021/jo302443k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efforts to substitute the cyclopropane ring in a series of aryl cyclopropylnitriles led to the discovery of an operationally simple one-pot method for Knoevenagel condensation and subsequent Corey-Chaykovsky cyclopropanation giving diastereomerically pure products as a racemic mixture of enantiomers. Method development and results for variably substituted aryl acetonitriles and aldehydes in the reaction are reported. A concise synthesis of (+/-)-bicifadine in two steps is provided to demonstrate the utility of the method.

引用

页码：780 / 785

页数：6

共 25 条

[1] REACTION OF VINYL SULFONE WITH ALPHA-METALLATED NITRILES
AGAWA, T
YOSHIDA, Y
KOMATSU, M
OHSHIRO, Y
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (03): : 751 - 755
[2] Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis
Aggarwal, VK
Winn, CL
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) : 611 - 620
[3] One-pot cyclization of dilithiated nitriles with isothiocyanates and epibromohydrin. Synthesis of 2-cyano-1-(hydroxymethyl)cyclopropanes and 2-cyanomethylidene-4-(hydroxymethyl)thiazolidines
Albrecht, Uwe
Freifeld, Ilia
Reinke, Helmut
Langer, Peter
[J]. TETRAHEDRON, 2006, 62 (24) : 5775 - 5786
[4] Bryson T., 1992, SYNLETT, P723
[5] Efficient and practical syntheses of a stable labelled form of the non-narcotic analgesic, bicifadine and its metabolites
Chen, Zhengming
Yang, Ji
Little, Gillian
Keats, Andrew
[J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2007, 50 (1-2) : 97 - 104
[6] Stereoselective construction of nitrile-substituted cyclopropanes
Denton, Justin R.
Cheng, Kevin
Davies, Huw M. L.
[J]. CHEMICAL COMMUNICATIONS, 2008, (10) : 1238 - 1240
[7] 1-ARYL-3-AZABICYCLO[3.1.0]HEXANES, A NEW SERIES OF NON-NARCOTIC ANALGESIC AGENTS
EPSTEIN, JW
BRABANDER, HJ
FANSHAWE, WJ
HOFMANN, CM
MCKENZIE, TC
SAFIR, SR
OSTERBERG, AC
COSULICH, DB
LOVELL, FM
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1981, 24 (05) : 481 - 490
[8] STEREOSELECTIVE SYNTHESIS OF VINYLCYCLOPROPANES FROM 2-PHENYLSULFONYL-1,3-CYCLOHEXADIENES AND KETONE ENOLATES OR NITRILE ANION
ERICSSON, AM
PLOBECK, NA
BACKVALL, JE
[J]. ACTA CHEMICA SCANDINAVICA, 1994, 48 (03): : 252 - 257
[9] 25 YEARS OF DIMETHYLSULFOXONIUM METHYLIDE (COREYS REAGENT)
GOLOLOBOV, YG
NESMEYANOV, AN
LYSENKO, VP
BOLDESKUL, IE
[J]. TETRAHEDRON, 1987, 43 (12) : 2609 - 2651
[10] SYNTHESIS AND REACTIONS OF A STABLE 2-SELENANAPHTHALENE, 1-CYANO-2-METHYL-2-SELENANAPHTHALENE
HORI, M
KATAOKA, T
SHIMIZU, H
TSUTSUMI, K
YOSHIMATSU, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) : 2458 - 2463

← 1 2 3 →