Enamine-Iminium Ion Nazarov Cyclization of α-Ketolenones

被引：71

作者：

Bow, William F.

Basak, Ashok K.

Jolit, Anais

Vicic, David A.

Tius, Marcus A. ^{[1
]}

机构：

[1] Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 03期

基金：

美国国家卫生研究院;

关键词：

ELECTROCYCLIZATION; DIENONES; ACIDS;

D O I：

10.1021/ol9025765

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mono-triflate salts of some chiral nonracemic 1,2-diamines react with alpha-ketoenones in a stoichiometric reaction to form products of the Nazarov cyclization in high enantiomeric ratios. The mechanism appears to involve rearrangement of an enamine-iminium ion.

引用

收藏

页码：440 / 443

页数：4

相关论文

共 39 条

[1] Catalytic asymmetric nazarov reactions promoted by chiral Lewis acid complexes [J].

Aggarwal, VK ;

Beffield, AJ .

ORGANIC LETTERS, 2003, 5 (26) :5075-5078

[2] Traceless Chiral Auxiliaries for the Allene Ether Nazarov Cyclization [J].

Banaag, April R. ;

Tius, Marcus A. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) :8133-8141

[3] Interrupting the nazarov cyclization with indoles [J].

Basak, Ashok K. ;

Tius, Marcus A. .

ORGANIC LETTERS, 2008, 10 (18) :4073-4076

[4] Formal Synthesis of (±)-Roseophilin [J].

Bitar, Abdallah Y. ;

Frontier, Alison J. .

ORGANIC LETTERS, 2009, 11 (01) :49-52

[5] An improved chiral auxiliary for the allene ether version of the Nazarov cyclization [J].

delos Santos, Derrick B. ;

Banaag, April R. ;

Tius, Marcus A. .

ORGANIC LETTERS, 2006, 8 (12) :2579-2582

[6] Asymmetric amine-intercepted nazarov cyclization [J].

Dhoro, Francis ;

Kristensen, Tor E. ;

Stockmann, Vegar ;

Yap, Glenn P. A. ;

Tius, Marcus A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (23) :7256-+

[7] Chiral and achiral crystal structures [J].

Flack, HD .

HELVETICA CHIMICA ACTA, 2003, 86 (04) :905-921

[8] The Nazarov cyclization in organic synthesis. Recent advances [J].

Frontier, AJ ;

Collison, C .

TETRAHEDRON, 2005, 61 (32) :7577-7606

[9] Synthesis and Structure Revision of Nakiterpiosin [J].

Gao, Shuanhu ;

Wang, Oiaoling ;

Chen, Chuo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (04) :1410-+

[10] Interrupted nazarov reactions using dichlorocyclopropanes: A novel mode of arene trapping [J].

Grant, Tina N. ;

West, F. G. .

ORGANIC LETTERS, 2007, 9 (19) :3789-3792

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