Prev. Article Next Article Table of Contents

Article

Highly Enantioselective Cyanosilylation of Aldehydes Catalyzed by Novel β-Amino Alcohol−Titanium Complexes

Supporting Info

Yan Li,^† Bin He,^† Bo Qin,^† Xiaoming Feng,*^† and Guolin Zhang^‡

Key Laboratory of Green Chemistry & Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China

J. Org. Chem., 2004, 69 (23), pp 7910–7913

DOI: 10.1021/jo0488356

Publication Date (Web): October 14, 2004

†

College of Chemistry, Sichuan University, China.

Address correspondence to this author. Fax: +86(28) 85418249.

‡

Chengdu Institute of Biology, Chinese Academy of Sciences, China.

, xmfeng@scu.edu.cn

Abstract

The β-amino alcohol 1b−Ti(Oi-Pr)₄ complex has been shown to catalyze the enantioselective cyanosilylation of aldehydes efficiently. In the presence of 5 mol % of 1b−Ti(Oi-Pr)₄ complex catalyst, the aromatic, conjugated, heteroaromatic, and aliphatic aldehydes were converted to their corresponding trimethylsilyl ethers of cyanohydrins in 90−99% yields with up to 94% ee under mild conditions.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue November 12, 2004
Received July 9, 2004

Recommend & Share

Related Content

Enantioselective Cyanosilylation of Ketones by a Catalytic Double-Activation Method Employing Chiral Lewis Acid and Achiral N-Oxide CatalystsOrganic Letters
- Enantioselective Cyanosilylation of Ketones by a Catalytic Double-Activation Method Employing Chiral Lewis Acid and Achiral N-Oxide Catalysts
  Fuxue Chen, Xiaoming Feng, Bo Qin, Guolin Zhang, and Yaozhong Jiang
  Organic Letters 2003 5 (6), pp 949–952
  Abstract: Enantioselective addition of TMSCN to ketones is achieved by a catalytic double-activation method using 1a−Ti(IV) complex as the Lewis acid and achiral N-oxide 2 as the Lewis base to activate ketones and TMSCN, respectively.
  Abstract | Full Text HTML | Hi-Res PDF
Monodentate Non-C₂-symmetric Chiral N-Heterocyclic Carbene Complexes for Enantioselective Synthesis. Cu-Catalyzed Conjugate Additions of Aryl- and Alkenylsilylfluorides to Cyclic EnonesThe Journal of Organic Chemistry
- Monodentate Non-C₂-symmetric Chiral N-Heterocyclic Carbene Complexes for Enantioselective Synthesis. Cu-Catalyzed Conjugate Additions of Aryl- and Alkenylsilylfluorides to Cyclic Enones
  Kang-sang Lee and Amir H. Hoveyda
  The Journal of Organic Chemistry 2009 74 (12), pp 4455–4462
  Abstract: A new class of enantioselective conjugate addition (ECA) reactions that involve aryl- or alkenylsilyl fluoride reagents and are catalyzed by chiral non-C₂-symmetric Cu-based N-heterocyclic carbene (NHC) complexes are disclosed. Transformations have been ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Highly Enantioselective Cyanation of Aldehydes Catalyzed by a Multicomponent Titanium ComplexThe Journal of Organic Chemistry
- Highly Enantioselective Cyanation of Aldehydes Catalyzed by a Multicomponent Titanium Complex
  Shaohua Gou, Xiaohong Chen, Yan Xiong, and Xiaoming Feng
  The Journal of Organic Chemistry 2006 71 (15), pp 5732–5736
  Abstract: A new multicomponent bifunctional catalytic system based on a titanium complex was used for the efficient enantioselective cyanation of aldehydes. The catalyst was readily prepared from tetraisopropyl titanate (Ti(Oi-Pr)₄), (S)-6,6‘-dibromo-1,1‘-bi-2-...
  Abstract | Full Text HTML | Hi-Res PDF

Article

Highly Enantioselective Cyanosilylation of Aldehydes Catalyzed by Novel β-Amino Alcohol−Titanium Complexes