Practical synthesis of 2,5-disubstituted 1,3-dioxolane-4-ones and highly diastereoselective cis-2,5-disubstituted 1,3-dioxolane-4-ones from alpha-hydroxy acids catalyzed by N-triflylphosphoramide

Kucuk, Hatice

doi:10.1016/j.tetlet.2015.08.046

Practical synthesis of 2,5-disubstituted 1,3-dioxolane-4-ones and highly diastereoselective cis-2,5-disubstituted 1,3-dioxolane-4-ones from alpha-hydroxy acids catalyzed by N-triflylphosphoramide

Atıf İçin Kopyala

Kucuk H.

TETRAHEDRON LETTERS, cilt.56, sa.41, ss.5583-5586, 2015 (SCI-Expanded)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 56 Sayı: 41
Basım Tarihi: 2015
Doi Numarası: 10.1016/j.tetlet.2015.08.046
Dergi Adı: TETRAHEDRON LETTERS
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.5583-5586
İstanbul Üniversitesi Adresli: Evet

Özet

N-triflylphosphoramide (NTPA) was found to be an efficient Bronsted acid catalyst for the practical synthesis of 2,5-disubstituted 1,3-dioxolane-4-ones. Racemic and optically pure mandelic acid and lactic acid could be protected using several aldehydes in high selectivity and moderate yield in the presence of NTPA without azeotropic distillation or use of a dehydrating reagent. (C) 2015 Elsevier Ltd. All rights reserved.