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[2,3] Sigmatropic Wittig Rearrangement of Chiral Allyloxyacetaldehyde Hydrazones in the Diastereo‐ and Enantioselective Synthesis of Protected, γ,δ‐Unsaturated α‐Hydroxyaldehydes and Cyanohydrins
Author(s) -
Enders Dieter,
Backhaus Dirk,
Runsink Jan
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199420981
Subject(s) - enantioselective synthesis , sigmatropic reaction , enantiomer , wittig reaction , chemistry , stereochemistry , organic chemistry , catalysis
The polyfunctional chiral building blocks 1 (X = CHO, CN) are accessible by [2,3] sigmatropic Wittig rearrangements. They were synthesized in three or four steps (with purification of an intermediate by chromatography), some of which with syn/anti selectivities of >98% syn and enantiomeric excesses of 94–97%. R 1 = Me, Et, n Pr, i Pr; R 2 = H, Me.