Enantioselective synthesis of cyclic, quaternary oxonitriles
Yükleniyor...
Tarih
2010
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
American Chemical Society
Erişim Hakkı
info:eu-repo/semantics/embargoedAccess
Özet
Quaternary oxonitriles are stereoselectively generated from the union of five-, six-, and seven-membered
2-chloroalkenecarbonitriles with chiral alcohols via a Claisen rearrangement. The strategy rests on a new
conjugate addition-elimination of allylic alkoxides to 2-chlorocycloalkenecarbonitriles to afford substituted 2-alkoxyalkenenitriles. Subsequent thermolysis unmasks a cyclic oxonitrile while selectively
forming a new quaternary center with enantiomeric ratios typically greater than 9:1. The overall alkylation strategy addresses the challenge of enantioselectively generating hindered, quaternary centers while
simultaneously installing ketone, nitrile, and olefin functionalities.
Açıklama
Anahtar Kelimeler
Quaternary Oxonitriles, Enantioselective Synthesis
Kaynak
The Journal of Organic Chemistry
WoS Q Değeri
Scopus Q Değeri
Cilt
75
Sayı
21
Künye
Güneş, Y., Polat, M. F., Sahin, E., Fleming, F. F., & Altundas, R. (2010). Enantioselective synthesis of cyclic, quaternary oxonitriles. The Journal of organic chemistry, 75(21), 7092-7098.
