Synthesis of 4-Hydroxy-4H-chromenes by Reaction of Salicylic Aldehydes with Alkynals Catalyzed by Silyl Prolinol Ethers

被引：21

作者：

Aleman, Jose ^{[1
]}

Alvarado, Cuauhtemoc ^{[1
]}

Marcos, Vanesa ^{[1
]}

Nunez, Alberto ^{[1
]}

Garcia Ruano, Jose Luis ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ CI, E-28049 Madrid, Spain

来源：

SYNTHESIS-STUTTGART | 2011年 / 12期

关键词：

organocatalysis; proline; chromenes; asymmetric synthesis; aminocatalysis; BAYLIS-HILLMAN REACTION; ONE-POT ACCESS; ASYMMETRIC-SYNTHESIS; ALPHA; BETA-UNSATURATED ALDEHYDES; PART; FUNCTIONALIZATION; ORGANOCATALYSIS; FLAVONOIDS; 4H-CHROMENES; DERIVATIVES;

D O I：

10.1055/s-0030-1260020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report an oxa-Michael/Baylis-Hillman tandem reaction between salicylaldehydes and alk-2-ynals activated by silyl prolinol ethers, affording 2,3-disubstituted 4-hydroxy-4H-chromenes in good yields and enantiomeric ratios (up to 98:2).

引用

页码：1840 / 1846

页数：7

共 84 条

[31]

HUANG ZW, 2002, Patent No. 2002161245

[32] Dual catalyst control in the amino acid-peptide-catalyzed enantioselective Baylis-Hillman reaction [J].

Imbriglio, JE ;

Vasbinder, MM ;

Miller, SJ .

ORGANIC LETTERS, 2003, 5 (20) :3741-3743

[33] Nine-Step Enantioselective Total Synthesis of (+)-Minfiensine [J].

Jones, Spencer B. ;

Simmons, Bryon ;

MacMillan, David W. C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (38) :13606-+

[34] Asymmetric Baylis-Hillman Reaction: An Enchanting Expedition [J].

Krishna, Palakodety Radha ;

Sachwani, Rachna ;

Reddy, Purumandla Srinivas .

SYNLETT, 2008, (19) :2897-2912

[35] Reactivity of Allenylphosphonates toward Salicylaldehydes and Activated Phenols: Facile Synthesis of Chromenes and Substituted Butadienes [J].

Kumar, N. N. Bhuvan ;

Reddy, M. Nagarjuna ;

Swamy, K. C. Kumara .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5395-5404

[36] Rational Design of FRET-Based Ratiometric Chemosensors for in Vitro and in Cell Fluorescence Analyses of Nucleoside Polyphosphates [J].

Kurishita, Yasutaka ;

Kohira, Takahiro ;

Ojida, Akio ;

Hamachi, Itaru .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (38) :13290-13299

[37]

LABRIE F, 2010, Patent No. 2010145010

[38] Bioactive Constituents of the Stem Bark of Beilschmiedia zenkeri [J].

Lenta, Bruno Ndjakou ;

Tantangmo, Ferdinand ;

Devkota, Krishna Prasad ;

Wansi, Jean Duplex ;

Chouna, Jean Rodolphe ;

Soh, Rene Cosme Fongang ;

Neumann, Beate ;

Stammler, Hans-Georg ;

Tsamo, Etienne ;

Sewald, Norbert .

JOURNAL OF NATURAL PRODUCTS, 2009, 72 (12) :2130-2134

[39] Chiral diphenylprolinol TES ether promoted conjugate addition-aldol-dehydration reactions between α,β-unsaturated aldehydes and 2-N-protected amino benzaldehydes [J].

Li, Hao ;

Wang, Jian ;

Xie, Hexin ;

Zu, Liansuo ;

Jiang, Wei ;

Duesler, Eileen N. ;

Wang, Wei .

ORGANIC LETTERS, 2007, 9 (06) :965-968

[40] One-pot approach to chiral chromenes via enantioselective organocatalytic domino oxa-Michael-aldol reaction [J].

Li, Hao ;

Wang, Jian ;

E-Nunu, Timiyin ;

Zu, Liansuo ;

Jiang, Wei ;

Wei, Shaohua ;

Wang, Wei .

CHEMICAL COMMUNICATIONS, 2007, (05) :507-509

← 1 2 3 4 5 6 7 8 9 →