Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States.
Org Lett. 2013 May 3;15(9):2202-5. doi: 10.1021/ol400749e. Epub 2013 Apr 25.
Two concise methods for generating oxetan-3-ones from allenes are reported. The first method employs allene epoxidation, opening of the spirodiepoxide by a halide nucleophile, and then intramolecular displacement of a halide by an alkoxide. The second method involves allene epoxidation and then thermal rearrangement of the corresponding spirodiepoxide to oxetan-3-one. The two methods are complementary and stereochemically divergent. Computational analysis of the thermal rearrangement is also described.
报告了两种简洁的方法，可从丙二烯生成噁烷-3-酮。第一种方法采用丙二烯环氧化，由卤化物亲核试剂开环，然后卤化物通过烷氧基进行分子内取代。第二种方法涉及丙二烯环氧化，然后相应的螺环二环氧热重排为噁烷-3-酮。这两种方法是互补的，立体化学上是不同的。还描述了热重排的计算分析。
