Enantioselective Acyloin Rearrangement of Acyclic Aldehydes Catalyzed by Chiral Oxazaborolidinium Ion

被引：9

作者：

Cho, Soo Min ^{[1
]}

Lee, Si Yeon ^{[1
]}

Ryu, Do Hyun ^{[1
]}

机构：

[1] Sungkyunkwan Univ, Dept Chem, Suwon 16419, South Korea

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 04期

基金：

新加坡国家研究基金会;

关键词：

D O I：

10.1021/acs.orglett.1c00314

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic enantioselective acyloin rearrangement of acyclic aldehydes to synthesize highly optically active acyloin derivatives is described. In the presence of a chiral oxazabor-olidinium ion catalyst, the reaction provided chiral alpha-hydroxy aryl ketones in high yield (up to 95%) and enantioselectivity (up to 98% ee). In addition, the enantioselective acyloin rearrangement of alpha,alpha-dialkyl-alpha-siloxy aldehydes produced chiral alpha-siloxy alkyl ketones in high yield (up to 92%) with good enantioselectivity (up to 89% ee).

引用

页码：1516 / 1520

页数：5

共 46 条

[1] Readily Available Ruthenium Complex for Efficient Dynamic Kinetic Resolution of Aromatic α-Hydroxy Ketones [J].

Agrawal, Santosh ;

Martinez-Castro, Elisa ;

Marcos, Rocio ;

Martin-Matute, Belen .

ORGANIC LETTERS, 2014, 16 (08) :2256-2259

[2] Total synthesis of the hydroxyketone kurasoin A using asymmetric phase-transfer alkylation [J].

Andrus, Merritt B. ;

Hicken, Erik J. ;

Stephens, Jeffrey C. ;

Bedke, D. Karl .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (22) :8651-8654

[3] Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids [J].

Banwell, Martin G. ;

Ma, Xinghua ;

Taylor, Rebecca M. ;

Willis, Anthony C. .

ORGANIC LETTERS, 2006, 8 (21) :4959-4961

[4] Asymmetric catalysis.: Part 153:: Metal-catalysed enantioselective α-ketol rearrangement [J].

Brunner, H ;

Kagan, HB ;

Kreutzer, G .

TETRAHEDRON-ASYMMETRY, 2003, 14 (15) :2177-2187

[5] Migratory Aptitudes in Rearrangements of Destabilized Vinyl Cations [J].

Cleary, Sarah E. ;

Hensinger, Magenta J. ;

Qin, Zhi-Xin ;

Hong, Xin ;

Brewer, Matthias .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (23) :15154-15164

[6] Enantioselective Catalysis Based on Cationic Oxazaborolidines [J].

Corey, E. J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (12) :2100-2117

[7]

Corey E. J., 2009, ANGEW CHEM, V121, P2134

[8] Catalytic Asymmetric Acyloin Rearrangements of α-Ketols, α-Hydroxy Aldehydes, and α-Iminols by N,N′-Dioxide-Metal Complexes [J].

Dai, Li ;

Li, Xiangqiang ;

Zeng, Zi ;

Dong, Shunxi ;

Zhou, Yuqiao ;

Liu, Xiaohua ;

Feng, Xiaoming .

ORGANIC LETTERS, 2020, 22 (13) :5041-5045

[9] Asymmetric induction in methyl ketone aldol additions to α-alkoxy and α,β-bisalkoxy aldehydes:: A model for acyclic stereocontrol [J].

Evans, David A. ;

Cee, Victor J. ;

Siska, Sarah J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (29) :9433-9441

[10] BINOL-phosphoric acids-catalyzed furylogous pinacol rearrangement of 1-[5-(hydroxy-diaryl-methyl)-furan-2-yl]-cyclobutanols into spiro cyclopentanones [J].

Fei, Chengcheng ;

Liu, Jianchao ;

Peng, Hui ;

Jiang, Dingxin ;

Yin, Biaolin .

TETRAHEDRON, 2018, 74 (48) :6939-6945

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