Catalytic asymmetric cyclopropanation of enones with dimethyloxosulfonium methylide promoted by a La-Li3-(Biphenyldiolate)3+NaI complex

被引：88

作者：

Kakei, Hiroyuki ^{[1
]}

Sone, Toshihiko ^{[1
]}

Sohtome, Yoshihiro ^{[1
]}

Matsunaga, Shigeki ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 44期

关键词：

D O I：

10.1021/ja076797c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic asymmetric cyclopropanation of enones with dimethyloxosulfonium methylide using a La-Li3-(biphenyldiolate)3 + NaI complex is described. The present method is complementary to the previously reported catalytic enantioselective methods in terms of ylides used, and trans products were exclusively obtained in good yield (96-73%) and high enantioselectivity (99-84% ee). Use of biphenyldiol 1b-H2 and NaI additive was essential to achieve high enantioselectivity. Copyright © 2007 American Chemical Society.

引用

页码：13410 / 13411

页数：2

共 31 条

[1]

Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1433, DOI 10.1002/1521-3773(20010417)40:8<1433::AID-ANIE1433>3.0.CO

[2]

2-E

[3] Asymmetric cyclopropanation reaction under phase-transfer catalyzed conditions [J].

Arai, S ;

Nakayama, K ;

Ishida, T ;

Shioiri, T .

TETRAHEDRON LETTERS, 1999, 40 (22) :4215-4218

[4] Pinwheel-shaped heterobimetallic lanthanide alkali metal binaphtholates: Ionic size matters! [J].

Aspinall, HC ;

Bickley, JF ;

Dwyer, JLM ;

Greeves, N ;

Kelly, RV ;

Steiner, A .

ORGANOMETALLICS, 2000, 19 (25) :5416-5423

[5] Catalytic asymmetric cyclopropanation of allylic alcohols with titanium-TADDOLate: Scope of the cyclopropanation reaction [J].

Charette, AB ;

Molinaro, C ;

Brochu, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (49) :12168-12175

[6] DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS [J].

COREY, EJ ;

CHAYKOVSKY, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1353-+

[7] 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

[8]

Denmark SE, 1998, ANGEW CHEM INT EDIT, V37, P1149, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1149::AID-ANIE1149>3.0.CO

[9]

2-F

[10] Solution versus solid-state structure of ytterbium heterobimetallic catalysts [J].

Di Bari, L ;

Lelli, M ;

Pintacuda, G ;

Pescitelli, G ;

Marchetti, F ;

Salvadori, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (18) :5549-5558

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