[2,3] Sigmatropic Wittig Rearrangement of Chiral Allyloxyacetaldehyde Hydrazones in the Diastereo‐ and Enantioselective Synthesis of Protected, γ,δ‐Unsaturated α‐Hydroxyaldehydes and Cyanohydrins | Zendy

Enders Dieter | Zendy; Backhaus Dirk | Zendy; Runsink Jan | Zendy

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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.

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