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Organic synthesis using haloboration reaction XVIII. A stereoselective synthesis of β—mono- and β,β-disubstituted α,β-unsaturated esters

✍ Scribed by Naoko Yamashina; Satoshi Hyuga; Shoji Hara; Akira Suzuki

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
216 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

D-Mono-and p,P-disubstituted a,P-unsaturated esters can be prepared in good yields stereoselectively by the stepwise alkylation and alkoxycarbonylation of 2-bromo-l-alkenylboronates.

Recently, we have demonstrated that the stepwise cross-coupling reactions of 2-bromo-lalkenylboranes, readily obtained by the bromoboration reaction of I-alkynes, are effectively catalyzed by palladium complex, which provide convenient and selective methods for the syntheses of (E)-disubstituted alkenes*, trisubstituted alkenes?-, and a,@unsaturated ketones. 3 As an extension of that work, we wish to report here a new method for the stereoselective synthesis of p-mono-and P,P-disubstituted a,@

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