Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore.
Org Lett. 2011 Mar 4;13(5):1072-5. doi: 10.1021/ol103119u. Epub 2011 Jan 26.
Pyrrolidine derivatives were prepared in high diastereoselectivities and good yields via a [3 + 2] cycloaddition of a tert-butyldimethylsilyl protected carbohydrate-based allene with a diverse range of imines. The subsequent removal of the carbohydrate auxiliary afforded a variety of pyrrolidines with excellent enantioselectivities (up to 99% ee). Selective reduction of the pyrrolidines further demonstrated the potential of this strategy.
通过叔丁基二甲基硅基保护的基于碳水化合物的丙二烯与各种亚胺的[3 + 2]环加成反应，以高非对映选择性和良好的收率制备了吡咯烷衍生物。随后去除碳水化合物辅助基团，得到了具有优异对映选择性的各种吡咯烷（高达 99%ee）。吡咯烷的选择性还原进一步证明了该策略的潜力。
