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Optional Diastereo‐ and Enantioselective Synthesis of Vicinal threo ‐ or erythro ‐Dihydroxy Derivatives
Author(s) -
Mulzer Johann,
Kappert Michael,
Huttner Gottfried,
Jibril Ibrahim
Publication year - 1984
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.198407041
Subject(s) - diastereomer , enantioselective synthesis , vicinal , alkoxide , chemistry , stereochemistry , cleavage (geology) , organic chemistry , catalysis , biology , fracture (geology) , paleontology
A possibility of obtaining the desired diastereomer of compounds containing the 1,2‐di‐ O structural element was realized with the isopropylidene‐protected ( R )‐glyceraldehyde 1a . Compound 1a can be converted >90% threo ‐ or erythro ‐selectively into the β‐alkoxycarboxylates 2 / 3 . For the preparation of 2 , the method of choice is the addition of diallylzinc followed by Lemieux cleavage, whereas the best route from 1a to 3 is via the aryl ester 1b and the addition of alkoxide to 1b . 2 and 3 can be converted into the lactones 4 and 5 , respectively.