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Highly Enantioselective Synthesis of (E)-Allylic Alcohols^†

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Hsyueh-Liang Wu, Ping-Yu Wu, and Biing-Jiun Uang*

Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan, 300, Republic of China bjuang@mx.nthu.edu.tw

J. Org. Chem., 2007, 72 (15), pp 5935–5937

DOI: 10.1021/jo0709403

Publication Date (Web): June 27, 2007

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

The asymmetric addition of alkenylzincs to aromatic and α-branched aliphatic aldehydes catalyzed by 1 generated the corresponding (E)-allylic alcohols with >95% ee and good to excellent chemical yields, especially >99.5% ee was observed in the case of 4-CF₃-benzaldehyde. Notably, 1 is an effective ligand to catalyze the addition of disubstituted (R₂ = R₃ = ethyl) and bulky substituted (R₂ = H, R₃ = tert-butyl) alkenylzincs to benzaldehyde, affording the corresponding allylic alcohols both with 96% ee.

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

Catalytic Enantioselective Synthesis of Secondary Allylic Alcohols from Terminal Alkynes and Aldehydes via 1-Alkenylboron Reagents
Takashi Shono and Toshiro Harada
Organic Letters2010 12 (22), 5270-5273
- Catalytic Enantioselective Synthesis of Secondary Allylic Alcohols from Terminal Alkynes and Aldehydes via 1-Alkenylboron Reagents
  Takashi Shono and Toshiro Harada
  Organic Letters2010 12 (22), 5270-5273
  A practical one-pot method has been developed for preparing enantioenriched secondary allylic alcohols starting from terminal alkynes and aldehydes. Hydroboration of terminal alkynes with dicyclohexylborane and subsequent reaction of the resulting ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Asymmetric Addition of Dimethylzinc to α-Ketoesters Catalyzed by (−)-MITH
Hsyueh-Liang Wu, Ping-Yu Wu, Ying-Ying Shen and Biing-Jiun Uang
The Journal of Organic Chemistry2008 73 (16), 6445-6447
- Asymmetric Addition of Dimethylzinc to α-Ketoesters Catalyzed by (−)-MITH
  Hsyueh-Liang Wu, Ping-Yu Wu, Ying-Ying Shen and Biing-Jiun Uang
  The Journal of Organic Chemistry2008 73 (16), 6445-6447
  This investigation describes the catalytic asymmetric addition of dimethylzinc to α-ketoesters in the presence of (−)-MITH (5) and triethyl borate as an additive to give the corresponding chiral α-hydroxy esters with good yields and high ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links