Enantioselective Bromolactonization of Conjugated (Z)-Enynes

被引：301

作者：

Zhang, Wei ^{[1
]}

Zheng, Suqing ^{[1
]}

Liu, Na ^{[1
]}

Werness, Jenny B. ^{[2
]}

Guzei, Ilia A. ^{[2
]}

Tang, Weiping ^{[1
]}

机构：

[1] Univ Wisconsin, Sch Pharm, Madison, WI 53705 USA

[2] Univ Wisconsin, Dept Chem, Madison, WI 53705 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 11期

关键词：

BIFUNCTIONAL CINCHONA ORGANOCATALYSTS; ASYMMETRIC CATALYSIS; MICHAEL ADDITION; AMINE COMPLEXES; CHIRAL SOURCES; DERIVATIVES; ALKALOIDS; IODOLACTONIZATIONS; HALOCYCLIZATION; MALONATE;

D O I：

10.1021/ja100173w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalytic enantioselective syn-1,4-bromolactonization of conjugated (Z)-enynes was reported. Diastereomeric ratios >20:1 and up to 99% enantiomeric excesses were observed. Di-, tri-, and tetra-substituted bromoallenes were prepared together with lactone heterocycles efficiently and stereoselectively, Preliminary investigations Suggest that the chiral catalyst may serve as a bifunctional reagent by interacting with both a carboxylic acid nucleophile and NBS electrophile.

引用

收藏

页码：3664 / +

页数：4

相关论文

共 41 条

[1] Stronger bronsted acids [J].

Akiyama, Takahiko .

CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758

[2] Recent progress in chiral Bronsted acid catalysis [J].

Akiyama, Takahiko ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010

[3] Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts [J].

Connon, Stephen J. .

CHEMICAL COMMUNICATIONS, 2008, (22) :2499-2510

[4] The Design of Novel, Synthetically Useful (Thio)urea-Based Organocatalysts [J].

Connon, Stephen J. .

SYNLETT, 2009, (03) :354-376

[5] Mechanistic evaluation of the halocyclization of 4-penten-1-ol by some bis(2-substituted pyridine) and bis(2,6-disubstituted pyridine)bromonium triflates [J].

Cui, XL ;

Brown, RS .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18) :5653-5658

[6] On the Absolute Configurational Stability of Bromonium and Chloronium Ions [J].

Denmark, Scott E. ;

Burk, Matthew T. ;

Hoover, Andrew J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) :1232-+

[7] SYNTHESIS AND SYNTHETIC UTILITY OF HALOLACTONES [J].

DOWLE, MD ;

DAVIES, DI .

CHEMICAL SOCIETY REVIEWS, 1979, 8 (02) :171-197

[8] Small-molecule H-bond donors in asymmetric catalysis [J].

Doyle, Abigail G. ;

Jacobsen, Eric N. .

CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743

[9] An approach to enantioselective 5-endo halo-lactonization reactions [J].

Garnier, Jean Marc ;

Robin, Sylvie ;

Rousseau, Gerard .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (20) :3281-3291

[10] The first reagent-controlled asymmetric halolactonizations. Dihydroquinidine-halogen complexes as chiral sources of positive halogen ion [J].

Grossman, RB ;

Trupp, RJ .

CANADIAN JOURNAL OF CHEMISTRY, 1998, 76 (09) :1233-1237

← 1 2 3 4 5 →