ChemInform Abstract: Controlled Synthesis of Regio‐, Enantio‐, and Diastereomers of Amino‐4‐pentenediols from 1,4‐Pentadien‐3‐ol via Epoxy‐4‐pentenols. Part 2. erythro‐ and threo‐3‐Amino‐4‐pentene‐1,2‐diols and erythro‐2‐Benzylamino‐4‐pentene‐1,3‐diol.

Jaeger, V.; Stahl, U.; Huemmer, W.

doi:10.1002/chin.199219068

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“…Although the simplest unsaturated epoxide 2 can be prepared by SAE of 2,4-pentadien-1-ol ( 3 ), a more convenient route is the kinetic resolution methodology developed by Jagger et al [ 12 , 13 , 14 ]. This entails SAE of 1,4-pentadien-3-ol ( 4 ) to give epoxide 5 in excellent enantiomeric excess (>99%), followed by Payne rearrangement [ 15 ] of 5 with NaOH 1M to afford 2 (60%).…”

Section: Synthesis Of Chiral Epoxy Alcoholsmentioning

confidence: 99%

Synthetic Applications of Chiral Unsaturated Epoxy Alcohols Prepared by Sharpless Asymmetric Epoxidation

Riéra

Moreno

2010

Molecules

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An overview of the synthesis and applications of chiral 2,3-epoxy alcohols containing unsaturated chains is presented. One of the fundamental synthetic routes to these compounds is Sharpless asymmetric epoxidation, which is reliable, highly chemoselective and enables easy prediction of the product enantioselectivity. Thus, unsaturated epoxy alcohols are readily obtained by selective oxidation of the allylic double bond in the presence of other carbon-carbon double or triple bonds. The wide availability of epoxy alcohols with unsaturated chains, the versatility of the epoxy alcohol functionality (e.g. regio- and stereo-selective ring opening; oxidation; and reduction), and the arsenal of established alkene chemistries, make unsaturated epoxy alcohols powerful starting materials for the synthesis of complex targets such as biologically active molecules. The popularization of ring-closing metathesis has further increased their value, making them excellent precursors to cyclic compounds.

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