β-Isocupreidine-Catalyzed Baylis−Hillman Reaction of Chiral N-Boc-α-Amino Aldehydes
Organic Letters2006Vol. 8(23), pp. 5357–5360
Citations Over TimeTop 10% of 2006 papers
Abstract
[Structure: see text] Beta-isocupreidine (beta-ICD)-catalyzed Baylis-Hillman reaction of chiral N-Boc-alpha-amino aldehydes and 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) takes place without racemization and exhibits the match-mismatch relationship between the substrate and the catalyst. In the case of acyclic amino aldehydes, L-substrates show excellent syn selectivity and high reactivity in contrast to D-substrates. On the other hand, in the case of cyclic amino aldehydes, D-substrates rather than L-substrates show excellent anti selectivity and high reactivity.
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