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Stereoselective synthesis of alcohols, XXXI: Stereoselective CC bond formation using chiral Z ‐pentenylboronates
Author(s) -
Hoffmann Reinhard W.,
Ditrich Klaus,
Köster Gerhard,
Stürmer Rainer
Publication year - 1989
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19891220926
Subject(s) - stereocenter , chemistry , stereoselectivity , benzaldehyde , reagent , stereospecificity , chirality (physics) , chiral auxiliary , alcohol , stereochemistry , double bond , enantioselective synthesis , medicinal chemistry , organic chemistry , catalysis , chiral symmetry , physics , quantum mechanics , quark , nambu–jona lasinio model
Using 1,2‐dicyclohexyl‐1,2‐ethanediol as chiral auxiliary, the enatiomerically pure Z ‐pentenylboronate 9c was obtained. Its addition to benzaldehyde proceeded with complete transfer of chirality to give the syn ‐ E ‐homoallyl alcohol 11 . The ability of the reagent 9c to create new stereocenters under reagent control of diastereoselectivity was tested in its addition to the chiral aldehydes 15 and 24 . This resulted in a short and stereospecific synthesis of invictolide ( 18 ), as well as of a C‐9/C‐15‐partial structure 25 of erythronolide A.