ISSN:
0009-2940
Keywords:
Dichloroketene
;
Stereoselective ketone reduction
;
Mitsunobu reaction
;
Cyclobutyl bromides
;
Cross-coupling reaction
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Stereoselective Synthesis of 3-Substituted Cyclobutanols and Products Derived Therefrom3-Substituted cyclobutanones 2 are prepared by alkene/dichloroketene cycloadditions and subsequent dehalogenation. Reduction with LiAlH(OtBu)3 furnishes cis-cyclobutanols 3 in 95-100% selectivity. Mitsunobu inversion turned out to be the only practical method to get trans isomers 4 in high selectivity. A stereoselective cyclobutanol→bromocyclobutane conversion could be achieved only by a modified Mitsunobu reaction. Cross coupling between zinc derivatives of bromocyclobutanes 9 and aromatic bromides is not stereoselective.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931261228
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