Expanding the Scope of the Direct Regiospecific Asymmetric Aldol Reaction to Enones and Dienones Catalyzed by a BINOL-Derived Bronsted Acid

被引：12

作者：

Das, Joydeb ^{[1
]}

Le Cavelier, Fabien ^{[1
]}

Rouden, Jacques ^{[1
]}

Blanchet, Jerome ^{[1
]}

机构：

[1] Univ Caen, Lab Chim Mol & Thioorgan, ENSICAEN, INC3M FR 3038,UMR CNRS 6507, F-14050 Caen, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 33期

关键词：

Organocatalysis; Aldol reactions; Bronsted acids; Enones; Asymmetric synthesis; PHOSPHORIC-ACIDS; ALDEHYDES; KETONES; YNONES;

D O I：

10.1002/ejoc.201101282

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral phosphoric acid (R)-1a has been shown to be an efficient Bronsted acid catalyst for the useful asymmetric synthesis of various acyclic and endo- and exocyclic beta-hydroxyenones through a regiospecific aldol reaction between alpha,beta-unsaturated ketones and ethyl glyoxalate. Moreover, two unprecedented examples involving sensitive dienones are reported.

引用

页码：6628 / 6631

页数：4

共 39 条

[31] Efficient Asymmetric Total Syntheses of Cryptocarya Triacetate, Cryptocaryolone, and Cryptocaryolone Diacetate [J].

Wang, Xiaolei ;

Wang, Wenkuan ;

Zheng, Huaiji ;

Su, Yingpeng ;

Jiang, Tuo ;

He, Yongping ;

She, Xuegong .

ORGANIC LETTERS, 2009, 11 (14) :3136-3138

[32]

Whalen LJ, 2006, ALDRICHIM ACTA, V39, P63

[33] Optically Active 1,1′-Spirobiindane-7,7′-diol (SPINOL)-Based Phosphoric Acids as Highly Enantioselective Catalysts for Asymmetric Organocatalysis [J].

Xing, Chun-Hui ;

Liao, Yuan-Xi ;

Ng, Jaclynn ;

Hu, Qiao-Sheng .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (10) :4125-4131

[34] SPINOL-Derived Phosphoric Acids: Synthesis and Application in Enantioselective Friedel-Crafts Reaction of Indoles with Imines [J].

Xu, Fangxi ;

Huang, Dan ;

Han, Chao ;

Shen, Wei ;

Lin, Xufeng ;

Wang, Yanguang .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (24) :8677-8680

[35] Direct catalytic asymmetric aldol reactions promoted by a novel barium complex [J].

Yamada, YMA ;

Shibasaki, M .

TETRAHEDRON LETTERS, 1998, 39 (31) :5561-5564

[36] Direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones [J].

Yamada, YMA ;

Yoshikawa, N ;

Sasai, H ;

Shibasaki, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (17) :1871-1873

[37] Direct catalytic asymmetric aldol reaction [J].

Yoshikawa, N ;

Yamada, YMA ;

Das, J ;

Sasai, H ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (17) :4168-4178

[38] Chiral BINOL-derived phosphoric acids: privileged Bronsted acid organocatalysts for C-C bond formation reactions [J].

Zamfir, Alexandru ;

Schenker, Sebastian ;

Freund, Matthias ;

Tsogoeva, Svetlana B. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (23) :5262-5276

[39] Organocatalysis of asymmetric aldol reaction. Catalysts and reagents [J].

Zlotin, S. G. ;

Kucherenko, A. S. ;

Beletskaya, I. P. .

RUSSIAN CHEMICAL REVIEWS, 2009, 78 (08) :737-784

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