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Reactivity of ( R )‐2‐ tert ‐Butyldihydrooxazole Derivatives Prepared from Serine and Threonine: Novel, Versatile Chiral Building Blocks
Author(s) -
Seebach Dieter,
Stucky Gerhard
Publication year - 1988
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.198813511
Subject(s) - decarboxylation , acylation , threonine , serine , reactivity (psychology) , chemistry , stereoselectivity , catalysis , organic chemistry , stereochemistry , combinatorial chemistry , enzyme , medicine , alternative medicine , pathology
The unsaturated cyclic N,O ‐acetals 1 and 2 are promising starting materials for the synthesis of further valuable chiral intermediates. They were prepared from serine and threonine, respectively, by electrochemical decarboxylation. Acylation and addition reactions as well as catalytic hydrogenation were used to convert 1 and 2 into the mono‐, bi‐, and tricyclic compounds of type 3 , in a regio‐ and stereoselective fashion.