Chiral Holmium Complex-Catalyzed Diels-Alder Reaction of Silyloxyvinylindoles: Stereoselective Synthesis of Hydrocarbazoles

被引：58

作者：

Harada, Shinji ^{[1
]}

Morikawa, Takahiro ^{[1
]}

Nishida, Atsushi ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, Chiba 2608675, Japan

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 20期

关键词：

LEWIS-ACID CATALYSTS; ASYMMETRIC-SYNTHESIS; CARBODIENOPHILES; ORGANOCATALYSTS; CYCLOADDITIONS; POLYMERIZATION; STRYCHNINE; AMINATION; DIENES; ESTERS;

D O I：

10.1021/ol402559z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic and asymmetric cycloaddition between 3[1-(silyloxy)vinyl]indoles and electron-deficient olefins gave substituted hydrocarbazoles in up to 99% yield and 94% ee. This reaction was catalyzed by a novel chiral holmium(III) complex. Alkylation of the cycloadduct gave a tricyclic compound with four continuous chiral centers, one of which was a quaternary carbon.

引用

页码：5314 / 5317

页数：4

共 48 条

[1] Cationic yttrium methyl complexes as functional models for polymerization catalysts of 1,3-dienes
Arndt, S
Beckerle, K
Zeimentz, PM
Spaniol, TP
Okuda, J
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (45) : 7473 - 7477
[2] STEREOSELECTIVE PREPARATION OF TRI AND TETRACYCLIC AMINES AS POTENTIAL INTERMEDIATES IN ASPIDOSPERMA ALKALOID SYNTHESIS
AZZOUZI, A
PERRIN, B
SINIBALDI, ME
GRAMAIN, JC
LAVAUD, C
[J]. TETRAHEDRON LETTERS, 1993, 34 (34) : 5451 - 5454
[3] Synthesis, structure, and dynamics of tris(η5-cyclopentadienyl)lanthanides and bis(η5-cyclopentadienyl)[bis(trimethylsilyl)amido]cerium(III)
Baisch, Ulrich
Pagano, Sandro
Zeuner, Martin
Gunne, Joern Schmedt auf der
Oeckler, Oliver
Schnick, Wolfgang
[J]. ORGANOMETALLICS, 2006, 25 (12) : 3027 - 3033
[4] Lanthanide bis(trifluoromethanesulfonyl)amides, synthesis, characterization and catalytic activity
Baudry, DB
Dormond, A
Duris, F
Bernard, JM
Desmurs, JR
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2003, 121 (02) : 233 - 238
[5] A Short Formal Total Synthesis of Strychnine with a Samarium Diiodide Induced Cascade Reaction as the Key Step
Beemelmanns, Christine
Reissig, Hans-Ulrich
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (43) : 8021 - 8025
[6] STEREOCONTROLLED FORMATION OF OCTAHYDRO-1H-PYRROLO[2,3-D]CARBAZOLES BY REDUCTIVE CYCLIZATION - TOTAL SYNTHESIS OF (+-)-N-BENZYLASPIDOSPERMIDINE
BENCHEKROUNMOUNIR, N
DUGAT, D
GRAMAIN, JC
HUSSON, HP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (23) : 6457 - 6465
[7] Site selectivity of the Diels-Alder reactions of 3-[1-(tert-butyldimethylsilyloxy)vin-1-yl]furan and 3-(propen-2-yl)furan. Synthesis of 4-substituted benzofurans
Benitez, A
Herrera, FR
Romero, M
Talamas, FX
Muchowski, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (04) : 1487 - 1492
[8] Synthesis of substituted pyrrolo[3,4-a]carbazoles
Bleile, M
Wagner, T
Otto, HH
[J]. HELVETICA CHIMICA ACTA, 2005, 88 (11) : 2879 - 2891
[9] Organocatalytic Multiple Cascade Reactions: A New Strategy for the Construction of Enantioenriched Tetrahydrocarbazoles
Cao, Yi-Ju
Cheng, Hong-Gang
Lu, Liang-Qiu
Zhang, Ji-Ji
Cheng, Ying
Chen, Jia-Rong
Xiao, Wen-Jing
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (04) : 617 - 623
[10] Highly enantioselective electrophilic amination and michael addition of cyclic β-ketoesters induced by lanthanides and (S,S)-ip-pybox:: The mechanism
Comelles, Josep
Pericas, Alex
Moreno-Manas, Marcial
Vallribera, Adelina
Drudis-Sole, Gali
Lledos, Agusti
Parella, Teodor
Roglans, Anna
Garcia-Granda, Santiago
Roces-Fernandez, Laura
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (06) : 2077 - 2087

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