Diastereoselectivity in unusual intermolecular tandem Michael reactions

作者：Hughes Andrew B^*; Verdon Christopher M; White Jonathan M

来源：Tetrahedron, 2012, 68(7): 1979-1987.

DOI：10.1016/j.tet.2011.12.046

• Tandem Michael reaction
• Diastereoselective
• Dimeric adducts
• Tandem conjugate addition
• X-ray diffraction

Highly stereoselective consecutive or tandem Michael (MIMI) reactions are reported. A variety of initial nucleophiles react with chiral acylated 1,3-oxazolidin-2-ones to generate a reactive enolate. The enolate then reacts stereoselectively with a second equivalent of the acylated 1,3-oxazolidin-2-one to afford %26apos;dimeric%26apos; adducts. The adducts have three new contiguous stereogenic centers formed with a high level of control. Single crystal X-ray crystallographic analysis confirmed this controlled formation of novel tandem acyclic conjugate addition or MIMI products in several examples.

• 出版日期2012-2-18