Synthesis of α-conhydrine

A synthesis of α-conhydrine has been achieved from trans-(2 S,4 R)-4-hydroxyproline via diastereoselective Grignard addition, regioselective Baeyer–Villiger reaction, and ring-closing metathesis as the key steps. [Display omitted]

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Bibliographic Details
Published inTetrahedron Vol. 62; no. 47; pp. 10843 - 10848
Main Authors Chang, Meng-Yang, Kung, Yung-Hua, Chen, Shui-Tein
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 20.11.2006
Elsevier
Subjects
Chemistry
Chemistry, Organic
Grignard addition
Physical Sciences
Regioselective Baeyer–Villiger reaction
Ring-closing metathesis
Science & Technology
trans-(2 S,4 R)-4-Hydroxyproline
α-Conhydrine
Regioselective Baeyer–Villiger reaction
Ring-closing metathesis
α-Conhydrine
trans-(2 S,4 R)-4-Hydroxyproline
Grignard addition
ASYMMETRIC-SYNTHESIS
FORMAL SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
ENANTIOSPECIFIC SYNTHESIS
alpha-conhydrine
trans-(2S,4R)-4-hydroxyproline
(+)-ALPHA-CONHYDRINE
EQUIVALENTS
ring-closing metathesis
DIASTEREOISOMERS
regioselective Baeyer-Villiger reaction
STEREOSELECTIVE-SYNTHESIS
ALKALOIDS
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Summary:A synthesis of α-conhydrine has been achieved from trans-(2 S,4 R)-4-hydroxyproline via diastereoselective Grignard addition, regioselective Baeyer–Villiger reaction, and ring-closing metathesis as the key steps. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.09.004