Enantioselective cyclocarbonylation of 2-vinylanilines to six-membered ring lactams

被引：52

作者：

Dong, C ^{[1
]}

Alper, H ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem, Ctr catalysis Res & Innovat, Ottawa, ON K1N 6N5, Canada

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 01期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/j.tetasy.2003.08.045

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A catalyst system based on Pd(OAC)(2)/(2S,4S)-(-)-4-diphenylphosphino-2-(diphenylphosphinomethyl)pyrrolidine has been found to effect asymmetric cyclocarbonylation of 2-vinylanilines to enantiomerically enriched six-membered ring lactams in excellent yield. The reaction was effected under an atmosphere of CO (500 psi) and H, (100 psi) in methylene chloride for 48 h; the chiral six-membered ring lactams were isolated in up to 98% yield and 84% ee. The stereoselectivity was influenced by the structure of the substrate and the reaction conditions. The enantiopurity of the lactam was further improved by recrystallization with 99% ee obtained in some cases. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：35 / 40

页数：6

共 46 条

[41] Innovative synthesis of 4-carbaldehydepyrrolin-2-ones by zwitterionic rhodium catalyzed chemo- and regioselective tandem cyclohydrocarbonylation/CO insertion of α-imino alkynes [J].

Van den Hoven, BG ;

Alper, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (42) :10214-10220

[42] PHOTOCHEMICAL APPROACH TO THE SYNTHESIS OF THE PYRROLO[1,4]BENZODIAZEPINE ANTIBIOTICS [J].

WEIDNERWELLS, MA ;

DECAMP, A ;

MAZZOCCHI, PH .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (24) :5746-5758

[43] First examples of enantioselective palladium-catalyzed thiocarbonylation of prochiral 1,3-conjugated dienes with thiols and carbon monoxide:: Efficient synthesis of optically active β,γ-unsaturated thiol esters [J].

Xiao, WJ ;

Alper, H .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) :6229-6233

[44] A novel synthetic route to chiral γ-lactams from α-amino acids via Rh-catalyzed intramolecular C-H insertion [J].

Yoon, CH ;

Flanigan, DL ;

Chong, BD ;

Jung, KW .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (18) :6582-6584

[45]

Yu WY, 1997, CHEM-EUR J, V3, P417

[46] PALLADIUM-CATALYZED VINYLIC SUBSTITUTION WITH HIGHLY ACTIVATED ARYL HALIDES [J].

ZIEGLER, CB ;

HECK, RF .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (15) :2941-2946

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