Diastereoselective Control Through Hydrogen Bonding in the Aziridination of the Chiral Allylic Alcohols by Acetoxyaminoquinazolinone
JOURNAL OF ORGANIC CHEMISTRY, cilt.74, sa.24, ss.9452-9459, 2009 (SCI-Expanded, Scopus)
- 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.