Diastereoselective Reduction of a Chiral N-Boc-Protected δ-Amino-α,β-unsaturated γ-Keto Ester Phe-Gly Dipeptidomimetic
- 26 November 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (26) , 9186-9191
- https://doi.org/10.1021/jo020442o
Abstract
The readily available N-Boc-protected delta-amino alpha,beta-unsaturated gamma-keto ester 1 was diastereoselectively reduced to the corresponding alcohols 2 and 3, using boron- and aluminum-based reducing reagents. Reduction reactions were successful and resulted in anti/syn ratios of alcohols of >95:5 (80% yield), using LiAlH(O-t-Bu)(3) in EtOH at -78 degrees C under chelation control, and 5:95 (98% yield), using NB-Enantride in THF at -78 degrees C under Felkin-Anh control.Keywords
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