Enantioselective Ir-Catalyzed Allylic Alkylation of Racemic Allylic Alcohols with Malonates

被引：13

作者：

Meng, Chun-Yan ^{[1
]}

Liang, Xiao ^{[1
]}

Wei, Kun ^{[1
]}

Yang, Yu-Rong ^{[1
]}

机构：

[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 03期

关键词：

ALPHA-ALLYLATION; IRIDIUM; ENANTIO; SUBSTITUTIONS; DIASTEREO; COMPLEX; AMINES; REGIO; ACID;

D O I：

10.1021/acs.orglett.8b04143

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ir-catalyzed enantioselective allylic alkylation of branched racemic allylic alcohols with malonates is described. Enabled by Carreira's chiral Ir/(P, olefin) complex, the method described allows allylic substitution with various aromatic alcohols and malonates with excellent enantioselectivity. The malonates could be used directly as efficient nucleophiles without the need of preactivation.

引用

页码：840 / 843

页数：4

共 45 条

[1] Very efficient phosphoramidite ligand for asymmetric iridium-catalyzed allylic alkylation [J].

Alexakis, A ;

Polet, D .

ORGANIC LETTERS, 2004, 6 (20) :3529-3532

[2] Formaldehyde N,N-Dialkylhydrazones as Neutral Formyl Anion Equivalents in Iridium-Catalyzed Asymmetric Allylic Substitution [J].

Breitler, Simon ;

Carreira, Erick M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (16) :5296-5299

[3] Diasteroselective and Enantioselective Ir-Catalyzed Allylic Substitutions of 1-Substituted 1-Fluoro-1-(arenesulfonyl)methylene Derivatives [J].

Chen, Jiteng ;

Zhao, Xiaoming ;

Dan, Wenyan .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (19) :10693-10698

[4] Iridium-Catalyzed Asymmetric Allylic Substitution Reactions [J].

Cheng, Qiang ;

Tu, Hang-Fei ;

Zheng, Chao ;

Qu, Jian-Ping ;

Helmchen, Guenter ;

You, Shu-Li .

CHEMICAL REVIEWS, 2019, 119 (03) :1855-1969

[5] Iridium-catalyzed enantioselective allylic substitutions with aliphatic nitro compounds as prenucleophiles [J].

Dahnz, A ;

Helmchen, G .

SYNLETT, 2006, (05) :697-700

[6] Iridium-catalyzed synthesis of primary allylic amines from allylic alcohols: Sulfamic acid as amonia equivalent [J].

Defieber, Christian ;

Ariger, Martin A. ;

Moriel, Patricia ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (17) :3139-3143

[7] Malononitrile as Acylanion Equivalent [J].

Foerster, Sebastian ;

Tverskoy, Olena ;

Helmchen, Guenter .

SYNLETT, 2008, (18) :2803-2806

[8] Enantioselective iridium-catalyzed allylic alkylations -: Improvements and applications based on salt-free reaction conditions [J].

Gnamm, Christian ;

Foerster, Sebastian ;

Miller, Nicole ;

Broedner, Kerstin ;

Helmchen, Guenter .

SYNLETT, 2007, (05) :790-794

[9] Enantio- and Diastereoselective Spiroketalization Catalyzed by Chiral Iridium Complex [J].

Hamilton, James Y. ;

Roessler, Simon L. ;

Carreira, Erick M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (24) :8082-8085

[10] Iridium-Catalyzed Enantioselective Allylic Alkynylation [J].

Hamilton, James Y. ;

Sarlah, David ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (29) :7532-7535

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