Enantioselective Reactions of Donor/Acceptor Carbenoids Derived from α-Aryl-α-Diazoketones

被引：89

作者：

Denton, Justin R. ^{[2
]}

Davies, Huw M. L. ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

[2] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 04期

基金：

美国国家科学基金会;

关键词：

C-H INSERTION; O-H; ASYMMETRIC-SYNTHESIS; SI-H; CYCLOPROPANATION; BONDS; CYCLOADDITIONS; DIAZOACETATES; CONSTRUCTION;

D O I：

10.1021/ol802614j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of a variety of a-aryl-a-diazo ketones with activated olefins, catalyzed by the adamantyl glycine-derived dirhodium complex Rh-2(S-PTAD)(4), generates cyclopropyl ketones with high diastereoselectivity (up to >95:5 dr) and enantioselectivity, (up to 98% ee). Intermolecular C-H functionalization of 1,4-cyclohexadiene by means of carbenoid-induced C-H insertion was also possible with this type of carbenoid.

引用

收藏

页码：787 / 790

页数：4

相关论文

共 40 条

[1] A stereospecific access to allylic systems using rhodium(II)-vinyl carbenoid insertion into Si-H, O-H, and N-H bonds [J].

Bulugahapitiya, P ;

Landais, Y ;

ParraRapado, L ;

Planchenault, D ;

Weber, V .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1630-1641

[2] Vinyldiazolactone as a vinylcarbene precursor: Highly selective C-H insertion and cyclopropanation reactions [J].

Bykowski, Darren ;

Wu, Kou-Hui ;

Doyle, Michael P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (50) :16038-16039

[3] Highly enantioselective insertion of carbenoids into o-h bonds of phenols:: An efficient approach to chiral α-aryloxycarboxylic esters [J].

Chen, Chao ;

Zhu, Shou-Fei ;

Liu, Bin ;

Wang, Li-Xin ;

Zhou, Qi-Lin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (42) :12616-+

[4] A novel stereocontrolled synthesis of 1,2-trans cyclopropyl ketones via Suzuki-type coupling of acid chlorides with cyclopropylboronic acids [J].

Chen, H ;

Deng, MZ .

ORGANIC LETTERS, 2000, 2 (12) :1649-1651

[5] CrCl2-promoted stereospecific and stereoselective alkyl- and silylcyclopropanation of α,β-unsaturated amides [J].

Concellon, Jose M. ;

Rodriguez-Solla, Humberto ;

Mejica, Carmen ;

Blanco, Elena G. ;

Garcia-Granda, Santiago ;

Diaz, M. Rosario .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (10) :3828-3836

[6] Synthetic and isolation studies related to the marine natural products (+)-elisabethadione and (+)-elisabethamine [J].

Dai, Xing ;

Wan, Zhongliang ;

Kerr, Russell G. ;

Davies, Huw M. L. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (06) :1895-1900

[7]

Davies H.M. L., 2001, ORG REACT, V57, P1, DOI DOI 10.1002/0471264180.OR057.01

[8] Stereoselectivity of methyl aryldiazoacetate cyclopropanations of 1,1-diarylethylene. Asymmetric synthesis of a cyclopropyl analogue of tamoxifen [J].

Davies, HML ;

Nagashima, T ;

Klino, JL .

ORGANIC LETTERS, 2000, 2 (06) :823-826

[9] Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid [J].

Davies, HML ;

Bruzinski, PR ;

Lake, DH ;

Kong, N ;

Fall, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) :6897-6907

[10] Effect of rhodium carbenoid structure on cyclopropanation chemoselectivity [J].

Davies, HML ;

Panaro, SA .

TETRAHEDRON, 2000, 56 (28) :4871-4880

← 1 2 3 4 →