Gold(I)-Catalyzed Dearomative Rautenstrauch Rearrangement: Enantioselective Access to Cyclopenta[b]indoles

被引：145

作者：

Zi, Weiwei ^{[1
]}

Wu, Hongmiao ^{[1
,2
]}

Toste, F. Dean ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

[2] Nanjing Univ, Sch Chem & Chem Engn, Inst Chem & BioMed Sci, Nanjing 210046, Jiangsu, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 09期

关键词：

ASYMMETRIC ALLYLIC DEAROMATIZATION; IMINO-NAZAROV CYCLIZATION; CATALYZED CYCLOISOMERIZATION; 3+2 CYCLOADDITION; PROPARGYLIC CARBOXYLATES; GOLD; CYCLOPROPANATION; ACETATES; ALKYNES;

D O I：

10.1021/jacs.5b00613

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly enantioselective dearomative Rautenstrauch rearrangement catalyzed by cationic (S)-DTBM-Segphosgold(I) is reported. This reaction provides a straightforward method to prepare enantioenriched cyclopenta[b]indoles. These: studies show vast difference in enantioselectivity in the reactions of propargyl acetates and propargyl acetals in the chiral ligand-controlled Rautenstrauch reaction.

引用

页码：3225 / 3228

页数：4

共 61 条

[1]

Alan D., 2015, CHEM SOC REV, V44, P677

[2] Asymmetric C2-C3 Cyclopentannulation of the Indole Ring [J].

Barluenga, Jose ;

Tudela, Eva ;

Ballesteros, Alfredo ;

Tomas, Miguel .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (06) :2096-+

[3]

Benitez D, 2009, NAT CHEM, V1, P482, DOI [10.1038/NCHEM.331, 10.1038/nchem.331]

[4] Gold-Catalyzed 1,3-Addition of a Sp3-Hybridized C-H Bond to Alkenylcarbenoid Intermediate [J].

Bhunia, Sabyasachi ;

Liu, Rai-Shung .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (49) :16488-+

[5] Nazarov Reactions of Vinyl Cyclopropylamines: An Approach to the Imino-Nazarov Problem [J].

Bonderoff, Sara A. ;

Grant, Tina N. ;

West, F. G. ;

Tremblay, Martin .

ORGANIC LETTERS, 2013, 15 (11) :2888-2891

[6] Enamine-Iminium Ion Nazarov Cyclization of α-Ketolenones [J].

Bow, William F. ;

Basak, Ashok K. ;

Jolit, Anais ;

Vicic, David A. ;

Tius, Marcus A. .

ORGANIC LETTERS, 2010, 12 (03) :440-443

[7] Enantioselective Gold(I)-Catalyzed Vinylogous [3+2] Cycloaddition between Vinyldiazoacetates and Enol Ethers [J].

Briones, John F. ;

Davies, Huw M. L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (36) :13314-13317

[8] Palladium(II)- and mercury(II)-catalyzed rearrangements of propargyl acetates [J].

Caruana, Patrick A. ;

Frontier, Alison J. .

TETRAHEDRON, 2007, 63 (43) :10646-10656

[9] Syntheses of 6-substituted truncated Yuehchukene analogues [J].

Cheng, KF ;

Cheung, MK ;

Kong, YC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1997, 50 (04) :349-353

[10] Recent advances in dearomatization of heteroaromatic compounds [J].

Ding, Qiuping ;

Zhou, Xiaoli ;

Fan, Renhua .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (27) :4807-4815

← 1 2 3 4 5 6 7 →