A useful and convenient synthetic protocol for interconversion of carbonyl compounds to the corresponding 1,3-oxathiolanes and vice versa employing organic ammonium tribromide (OATB)

• Published in: Tetrahedron letters Vol. 43; no. 15; pp. 2843 - 2846
• Main Authors: Mondal, Ejabul, Sahu, Priti Rani, Bose, Gopal, Khan, Abu T.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 08.04.2002; Elsevier
• Subjects: 1,3-oxathiolanes; cetyltrimethylammonium tribromide (CetTMATB); Chemistry; Chemistry, Organic; deprotection; n-tetrabutylammonium tribromide (TBATB); Physical Sciences; protection; Science & Technology; deprotection; 1,3-oxathiolanes; protection; n-tetrabutylammonium tribromide (TBATB); cetyltrimethylammonium tribromide (CetTMATB); REAGENT; MONOTHIOACETALS; CLEAVAGE; n-tetrabutylammonium; ENVIRONMENTALLY BENIGN SYNTHESIS; BROMIDE; tribromide (TBATB); EFFICIENT; DITHIOACETALS
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/S0040-4039(02)00345-3

A wide variety of carbonyl compounds 1 can be easily protected selectively as the corresponding 1,3-oxathiolanes 2 in good yields using a catalytic amount (0.01–0.1 equiv.) of n-tetrabutylammonium tribromide in dry CH 2Cl 2 at 0–5 °C. On the other hand, various 1,3-oxathiolanes 2 can be deprotected chemoselectively to the parent carbonyl compounds 1 employing 0.5 equivalents of organic ammonium tribromides under identical conditions in very high yields. Mild conditions, high selectivity and yield, highly efficient, less expensive, and no brominations either at the double bond or allylic position and even α- to the keto position or aromatic ring are some of the major advantages of the protocol. Graphic