Premium
Stereoselective Syntheses of Alcohols, XXXIII 1 Addition of E ‐ and Z ‐Pentenylboronates to Ketones
Author(s) -
Hoffmann Reinhard W.,
Sander Thomas
Publication year - 1990
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.19901230127
Subject(s) - chemistry , stereoselectivity , reagent , titanium , grignard reaction , grignard reagent , ketone , organic chemistry , aliphatic compound , medicinal chemistry , catalysis
The isomerically pure Z ‐ and E ‐pentenylboronates 2 and 3 were added to ketones under 4 to 8 kbar pressure resulting in the homoallyl alcohols 10‐13 with different diastereoselectivities. These reactions were considered as models for the addition of other Z‐ and E ‐pentenylmetal compounds to ketones. The diastereoselectivities obtained in the addition of the configurationally undefined pentenyl Grignard ( 4 ) and titanium reagents ( 5,6 ) is discussed against this background.