Enantioselective sp3 C-H alkylation of γ-butyrolactam by a chiral Ir(I) catalyst for the synthesis of 4-substituted γ-amino acids

被引：60

作者：

Tahara, Yu-ki ^{[1
]}

Michino, Masamichi ^{[1
]}

Ito, Mamoru ^{[1
]}

Kanyiva, Kyalo Stephen ^{[2
]}

Shibata, Takanori ^{[1
,3
]}

机构：

[1] Waseda Univ, Sch Adv Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, Japan

[2] Waseda Univ, ICSEP, Shinjuku Ku, Tokyo 1698555, Japan

[3] JST, ACT C, Kawaguchi, Saitama 3320012, Japan

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 93期

关键词：

ALPHA; GAMMA-CYCLIC PEPTIDES; BOND FUNCTIONALIZATION; AMINOBUTYRIC-ACID; ORGANIC-SYNTHESIS; HDAC INHIBITORS; NITROGEN ATOM; N-OXIDES; ACTIVATION; ALKENES; ANTICONVULSANT;

D O I：

10.1039/c5cc07102j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ir-catalyzed sp(3) C-H alkylation of gamma-butyrolactam with alkenes was used for the highly enantioselective synthesis of 5-substituted gamma-lactams, which were readily converted into chiral 4-substituted gamma-amino acids. A broad scope of alkenes was amenable as coupling partners, and the alkylated product using acrylate could be transformed into the key intermediate of pyrrolam A synthesis.

引用

页码：16660 / 16663

页数：4

共 79 条

[1] The smallest α,γ-peptide nanotubulet segments:: Cyclic α,γ-tetrapeptide dimers [J].

Amorín, M ;

Brea, RJ ;

Castedo, L ;

Granja, JR .

ORGANIC LETTERS, 2005, 7 (21) :4681-4684

[2] Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity [J].

Anderson, CE ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) :12412-12413

[3] γ-Amino Alcohols via Organocascade Reactions Involving Dienamine Catalysis [J].

Appayee, Chandrakumar ;

Fraboni, Americo J. ;

Brenner-Moyer, Stacey E. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (19) :8828-8834

[4] Control of helix formation in vinylogous γ-peptides by (E)- and (Z)-double bonds:: A way to ion channels and monomolecular nanotubes [J].

Baldauf, C ;

Günther, R ;

Hofmann, HJ .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) :5351-5361

[5] Catalytic Enantioselective Allylic Amination of Unactivated Terminal Olefins via an Ene Reaction/[2,3]-Rearrangement [J].

Bao, Hongli ;

Tambar, Uttam K. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (45) :18495-18498

[6] Large-diameter self-assembled dimers of α,γ-cyclic peptides, with the nanotubular solid-state structure of cyclo-[(L-Leu-D-MeN-γ-Acp)4-] 4CHCl2COOH [J].

Brea, Roberto J. ;

Castedo, Luis ;

Granja, Juan R. .

CHEMICAL COMMUNICATIONS, 2007, (31) :3267-3269

[7] Identification of novel ligands for the gabapentin binding site on the α2δ subunit of a calcium channel and their evaluation as anticonvulsant agents [J].

Bryans, JS ;

Davies, N ;

Gee, NS ;

Dissanayake, VUK ;

Ratcliffe, GS ;

Horwell, DC ;

Kneen, CO ;

Morrell, AI ;

Oles, RJ ;

O'Toole, JC ;

Perkins, GM ;

Singh, L ;

Suman-Chauhan, N ;

O'Neill, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (11) :1838-1845

[8] Highly Enantioselective γ-Amination by N-Heterocyclic Carbene Catalyzed [4+2] Annulation of Oxidized Enals and Azodicarboxylates [J].

Chen, Xiang-Yu ;

Xia, Fei ;

Cheng, Jin-Tang ;

Ye, Song .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (40) :10644-10647

[9] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].

Chen, Xiao ;

Engle, Keary M. ;

Wang, Dong-Hui ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115

[10] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].

Cho, Seung Hwan ;

Kim, Ji Young ;

Kwak, Jaesung ;

Chang, Sukbok .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083

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