Highly enantioselective [4+2]cycloaddition reactions catalyzed by a chiral N-methyl-oxazaborolidinium cation

被引：49

作者：

Canales, Eda ^{[1
]}

Corey, E. J. ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 15期

关键词：

D O I：

10.1021/ol8011502

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of lithium aryl borohydrides with salts of beta-amino alcohols provides a new route for the synthesis of oxazaborolidines. This method also leads to the first synthesis of hitherto elusive N-methyl oxazaborolidine cations, specifically the cationic proline derivative 3. Compound 3 is a strong chiral Lewis acid which is very effective for catalysis of [4 + 2]-cycloaddition reactions in good yield and with high enantioselectivity. Several diverse examples illustrate the scope of these catalytic reactions.

引用

页码：3271 / 3273

页数：3

共 17 条

[11] Broad-spectrum enantioselective Diels-Alder catalysis by chiral, cationic oxazaborolidines [J].

Ryu, DH ;

Lee, TW ;

Corey, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (34) :9992-9993

[12] ADDITION-COMPOUNDS OF ALKALI-METAL HYDRIDES .25. RAPID REACTION OF BORONIC ESTERS AND ACIDS WITH LITHIUM ALUMINUM-HYDRIDE - A NOVEL AND QUANTITATIVE SYNTHESIS OF LITHIUM MONOORGANYLBOROHYDRIDES [J].

SINGARAM, B ;

COLE, TE ;

BROWN, HC .

ORGANOMETALLICS, 1984, 3 (05) :774-777

[13] Concise total syntheses of palominol, dolabellatrienone, β-araneosene, and isoedunol via an enantioselective Diels-Alder macrobicyclization [J].

Snyder, SA ;

Corey, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (03) :740-742

[14] Conversion of Torgov's synthesis of estrone into a highly enantioselective and efficient process [J].

Yeung, Ying-Yeung ;

Chein, Rong-Jie ;

Corey, E. J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (34) :10346-+

[15] A short enantioselective pathway for the synthesis of the anti-influenza neuramidase inhibitor Oseltamivir from 1,3-butadiene and acrylic acid [J].

Yeung, Ying-Yeung ;

Hong, Sungwoo ;

Corey, E. J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (19) :6310-6311

[16] Short, enantioselective total synthesis of aflatoxin B2 using an asymmetric [3+2]-cycloaddition step [J].

Zhou, G ;

Corey, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (34) :11958-11959

[17] Useful enantioselective bicyclization reactions using an N-protonated chiral oxazaborolidine as catalyst [J].

Zhou, G ;

Hu, QY ;

Corey, EJ .

ORGANIC LETTERS, 2003, 5 (21) :3979-3982

← 1 2 →