Diastereoselective Control Through Hydrogen Bonding in the Aziridination of the Chiral Allylic Alcohols by Acetoxyaminoquinazolinone

ÇAKICI, Murat; Karabuga, Semistan; KILIÇ, Hamdullah; Ulukanli, Sabri; ŞAHİN, Ertan; Sevin, Fatma

doi:10.1021/jo902092s

Diastereoselective Control Through Hydrogen Bonding in the Aziridination of the Chiral Allylic Alcohols by Acetoxyaminoquinazolinone

Atıf İçin Kopyala

ÇAKICI M., Karabuga S., KILIÇ H., Ulukanli S., ŞAHİN E., Sevin F.

JOURNAL OF ORGANIC CHEMISTRY, cilt.74, sa.24, ss.9452-9459, 2009 (SCI-Expanded)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 74 Sayı: 24
Basım Tarihi: 2009
Doi Numarası: 10.1021/jo902092s
Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.9452-9459
Atatürk Üniversitesi Adresli: Evet

Özet

A high diastereoselectivity (up to > 99:1) is found for the aziridinations of chiral allylic alcohols with acetoxyaminoquinazolinone (Q-NHOAc). The selectivity is explained in terms of hydrogen bonding between the hydroxy functionality of the allylic alcohol and the remote carbonyl group of the quinazolinone.