A phosphine-catalyzed [3+6] annulation reaction of modified allylic compounds and tropone

被引：186
作者：
Du, YH [1 ]
Feng, JQ [1 ]
Lu, XY [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 10期
关键词：
D O I：
10.1021/ol050443d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel phosphine-catalyzed reaction of modified allylic compounds, including acetates, bromides, chlorides, or tert-butyl carbonates derived from the Morita-Baylis-Hillman (MBH) reaction with tropone to yield [3+6] annulation products in excellent yields was developed. It offers a simple and convenient method for constructing bridged nine-membered carbocycles.
引用
收藏
页码：1987 / 1989
页数：3
相关论文
共 39 条
[1]   NORMAL VS ABNORMAL NUCLEOPHILIC SUBSTITUTIONS ON CYCLOHEPTATRIENONES CARRYING A MOBILE ALPHA SUBSTITUENT - RATIONALIZATION [J].
BIGGI, G ;
DELCIMA, F ;
PIETRA, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (21) :7101-7107
[2]   An intramolecular organocatalytic cyclopropanation reaction [J].
Bremeyer, N ;
Smith, SC ;
Ley, SV ;
Gaunt, MJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (20) :2681-2684
[3]   Phosphine-catalyzed regiospecific allylic amination and dynamic kinetic resolution of Morita-Baylis-Hillman acetates [J].
Cho, CW ;
Kong, JR ;
Krische, MJ .
ORGANIC LETTERS, 2004, 6 (08) :1337-1339
[4]   A catalytic carbon-phosphorus ylide reaction: Phosphane-catalyzed annulation of allylic compounds with electron-deficient alkenes [J].
Du, YH ;
Lu, XY ;
Zhang, CM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (09) :1035-+
[5]   Alkaloids-catalyzed regio- and enantioselective allylic nucleophilic substitution of tert-butyl carbonate of the Morita-Baylis-Hillman products [J].
Du, YS ;
Han, XL ;
Lu, XY .
TETRAHEDRON LETTERS, 2004, 45 (25) :4967-4971
[6]   A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol [J].
Du, YS ;
Lu, XY .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6463-6465
[7]   Highly regioselective construction of spirocycles via phosphine-catalyzed [3+2]-cycloaddition [J].
Du, YS ;
Lu, XY ;
Yu, YH .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8901-8905
[8]   The vinylogous intramolecular Morita-Baylis-Hillman reaction: Synthesis of functionalized cyclopentenes and cyclohexenes with trialkylphosphines as nucleophilic catalysts [J].
Frank, SA ;
Mergott, DJ ;
Roush, WR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (11) :2404-2405
[9]   INTRAMOLECULAR [6+4] AND [4+2] TROPONE OLEFIN CYCLOADDITION REACTIONS - FACILE SYNTHESIS OF THE INGENANE RING-SYSTEM [J].
FUNK, RL ;
BOLTON, GL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) :4655-4657
[10]   PERISELECTIVITIES IN THERMAL ADDITION OF TROPONE TO ALLENIC ESTERS [J].
GANDHI, RP ;
ISHAR, MPS .
CHEMISTRY LETTERS, 1989, (01) :101-104
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