Lewis acid-catalyzed reactions of oxiranes with a variety of C=S compounds yield 1,3-oxathiolanes. The ring enlargement of monosubstituted oxiranes occurs regioselectively via cleavage of the O,C(3) bond of alkyl substituted oxiranes and the O,C(2) bond of phenyl oxirane. Furthermore, the reaction proceeds with inversion of the configuration at the center of the nucleophilic attack by the S-ato...

2.7. Redox Deprotections 221 3. Thiol Protecting Groups 223 4. Carboxy Protecting Groups 223 4.1. Protection 224 4.2. Deprotection 226 5. Carbonyl Protecting Groups 227 5.1. Acetals 227 5.1.1. Protection 227 5.1.2. Deprotection 231 5.2. Dithioacetals 233 5.2.1. Protection 233 5.2.2. Deprotection 235 5.3. 1,3-Oxathiolanes 237 5.4. 1,1-Diacetates (Acylals) 238 5.4.1. Protection 238 5.4.2. Deprote...

In this project various types of carbonyl compounds were efficiently converted to their corresponding 1,3-oxathiolanes  with 2-mercaptoethanol in the presence of catalytic amount of Al-MCM-41 with microwave energy. The catalyst can be reused several times without loss of its catalytic activity. Very short reaction times, reusability of the catalyst, and easy workup are noteworthy advantages of ...

The reaction of a rhodanine derivative (= (Z)-5-benzylidene-3-phenyl-2-thioxo-1,3-thiazolidin4-one; 1) with (S)-2-methyl-oxirane (2) in the presence of SiO2 in dry CH2Cl2 for 10 days led to two diastereoisomeric spirocyclic 1,3-oxathiolanes 3 and 4 with the Me group at C(2) (Scheme 2). The analogous reaction of 1 with (R)-2-phenyloxirane (5) afforded also two diastereoisomeric spirocyclic 1,3ox...