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Stereoselective Synthesis of Alcohols, XX. Diastereoselective Addition of γ‐Alkoxyallylboronates to Aldehydes
Author(s) -
Hoffmann Reinhard W.,
Kemper Bruno,
Metternich Rainer,
Lehmeier Thomas
Publication year - 1985
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198519851115
Subject(s) - chemistry , stereoselectivity , adduct , alkoxy group , diol , stereochemistry , medicinal chemistry , organic chemistry , catalysis , alkyl
Both the ( Z )‐ and the ( E )‐γ‐alkoxy‐substituted allylboronates 1 and 3 have been prepared. They add to aldehydes with a diastereoselectivity generally exceeding 90% to give the syn ‐ ( 2 ) and anti ‐diol derivatives 4 , respectively. The structure of one of these adducts has been established by conversion into exo ‐brevicomin ( 26 ).
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