Highly diastereoselective and enantioselective direct organocatalytic anti-selective Mannich reactions employing N-tosylimines

Lili Cheng; Xiao Han; Huiming Huang; Ming Wah Wong; Yixin Lu

doi:10.1039/B706793C

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Chemical Communications

Issue 40, 2007

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Highly diastereoselective and enantioselective direct organocatalytic anti-selective Mannich reactions employing N-tosylimines

Lili Cheng , Xiao Han , Huiming Huang , Ming Wah Wong and Yixin Lu

Chem. Commun., 2007, 4143-4145

DOI: 10.1039/B706793C
Received 08 May 2007, Accepted 09 Jul 2007
First published on the web 03 Aug 2007

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Organocatalytic direct anti-selective Mannich reactions of O-TBS-hydroxyacetone with various N-tosylimines derived from aromatic aldehydes in the presence of L-threonine-derived catalyst afforded 1,2-amino alcohols in good yields and with enantioselectivities of 99% in almost all cases.

Abstract from Methods in Organic Synthesis 2008

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Experimental, characterisation of products and Cartesian coordinates of the optimized (HF/3-21G) anti-transition state
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Lili Cheng
Xiao Han
Huiming Huang
Ming Wah Wong
Yixin Lu

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Chemical Communications

Highly diastereoselective and enantioselective direct organocatalytic anti-selective Mannich reactions employing N-tosylimines

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