SYNTHESIS OF 2-SUBSTITUTED DIHYDROPYRAN 3-O-CARBAMATES VIA COMBINED METALATION-SUZUKI-MIYAURA CROSS-COUPLING REACTIONS

Authors
BOWER JF GUILLANEUX D NGUYEN T WONG PL SNIECKUS V
Citation
Jf. Bower et al., SYNTHESIS OF 2-SUBSTITUTED DIHYDROPYRAN 3-O-CARBAMATES VIA COMBINED METALATION-SUZUKI-MIYAURA CROSS-COUPLING REACTIONS, Journal of organic chemistry, 63(5), 1998, pp. 1514-1518
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
5
Year of publication
1998
Pages
1514 - 1518
Database
ISI
SICI code
0022-3263(1998)63:5<1514:SO2D3V>2.0.ZU;2-Z
Abstract
Treatment of 6-[(N,N-diethylcarbamoyl)oxy]-3,4-dihydro-2H-pyran (8) wi th t-BuLi followed by quench with a variety of electrophiles leads to 2-substituted products 9a-j (Table 2) in modest to good yields. The th ereby obtained 2-boronic acid (11) and iodo (9j) derivatives undergo S uzuki-Migaura cross-coupling reactions to afford 2-aryl and -heteroary l dihydropyran O-carbamates 12a-d in excellent yields.