Cu(I)-NHC Catalyzed Asymmetric Silyl Transfer to Unsaturated Lactams and Amides

被引：83

作者：

Pace, Vittorio ^{[1
]}

Rae, James P. ^{[1
]}

Procter, David J. ^{[1
]}

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 02期

基金：

英国工程与自然科学研究理事会;

关键词：

SI-B BOND; CONJUGATE ADDITION; ORGANIC-SYNTHESIS; PHENYLDIMETHYLSILYL GROUP; ALPHA; BETA-UNSATURATED ACCEPTORS; ENANTIOSELECTIVE SYNTHESIS; SILAFUNCTIONAL COMPOUNDS; SAMARIUM(II) IODIDE; CARBON BOND; SILICON;

D O I：

10.1021/ol4033623

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first asymmetric silylation of unsaturated lactams and amides using Cu(I)-NHC catalysts and PhMe(2)SiBpin has been accomplished. The method has been exploited in an expedient asymmetric synthesis of the (R)-enantiomer of the nootropic drug oxiracetam.

引用

页码：476 / 479

页数：4

共 67 条

[1] SILICON-BASED PROTECTING GROUP FOR ALPHA-BETA-UNSATURATION OF ALPHA-BETA-UNSATURATED KETONES
AGER, DJ
FLEMING, I
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (04) : 177 - 178
[2] Stereocontrol in organic synthesis using silicon-containing compounds. A synthesis of methyl (+)-nonactate
Ahmar, M
Duyck, C
Fleming, I
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (17): : 2721 - 2732
[3] Copper-free and copper-promoted conjugate addition reactions of bis(triorganosilyl) zincs and tris(triorganosilyl) zincates
Auer, Gertrud
Weiner, Barbara
Oestreich, Martin
[J]. SYNTHESIS-STUTTGART, 2006, (13): : 2113 - 2116
[4] Solvent applications of 2-methyltetrahydrofuran in organometallic and biphasic reactions
Aycock, David F.
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (01) : 156 - 159
[5] Fleming-Tamao oxidation and masked hydroxyl functionality: Total synthesis of (+)-pramanicin and structural elucidation of the antifungal natural product (-)-pramanicin
Barrett, AGM
Head, J
Smith, ML
Stock, NS
White, AJP
Williams, DJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) : 6005 - 6018
[6] Copper(II)-Catalyzed Silyl Conjugate Addition to α,β-Unsaturated Conjugated Compounds: Bronsted Base-Assisted Activation of Si-B Bond in Water
Calderone, Joseph A.
Santos, Webster L.
[J]. ORGANIC LETTERS, 2012, 14 (08) : 2090 - 2093
[7] Copper(I)-catalyzed disilylation of alkylidene malonates employing a Lewis base activation strategy
Clark, CT
Lake, JF
Scheidt, KA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (01) : 84 - 85
[8] Copper-Catalyzed Asymmetric Conjugate Addition of Alkenyl- and Alkylalanes to α,β-Unsaturated Lactams
Cottet, Pierre
Mueller, Daniel
Alexakis, Alexandre
[J]. ORGANIC LETTERS, 2013, 15 (04) : 828 - 831
[9] CONJUGATE ADDITION OF THE PHENYLDIMETHYLSILYL GROUP TO ALPHA-BETA-UNSATURATED CARBONYL-COMPOUNDS USING A SILYLZINCATE IN-PLACE OF THE SILYLCUPRATE
CRUMP, RANC
FLEMING, I
URCH, CJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (06): : 701 - 706
[10] Conjugate additions of a simple monosilylcopper reagent with use of the CuI•DMS complex:: Stereoselectivities and a dramatic impact by DMS
Dambacher, J
Bergdahl, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) : 580 - 589

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