Use of the thiophenesulfonyl protecting group in the catalytic, asymmetric synthesis of unprotected beta-lactams

作者：Wang Yazhong; Calter Michael A^*

来源：Tetrahedron Letters, 2015, 56(23): 3334-3336.

DOI：10.1016/j.tetlet.2015.01.108

• beta-Lactams
• Asymmetric catalysis
• Ketenes
• Protecting groups

We have found that the thiophenesulfonyl group is compatible with the catalytic, asymmetric synthesis of beta-lactams from acid chlorides and sulfonyl imines in the presence of a silylated cinchona alkaloid and tris(hexamethyl disilazide) lanthanide complex co-catalysts. The thiophenesulfonyl group can be subsequently removed in moderate yields without causing decomposition of the beta-lactam or lowering its stereochemical purity.

• 出版日期2015-6-3