A concise alpha-amino acid-based synthetic approach to [1,4]oxazepin-2-ones from Baylis-Hillman adducts

作者：Yadav Lal Dhar S^*; Srivastava Vishnu P; Patel Rajesh

来源：Tetrahedron Letters, 2009, 50(13): 1423-1426.

DOI：10.1016/j.tetlet.2009.01.048

• Baylis-Hillman adducts
• [1,4]Oxazepines
• Amino acids
• Nucleophilic substitution
• Michael-addition
• Cyclization reactions

An original two-step process for the synthesis of [1,4]oxazepin-2-ones starting from Baylis-Hillman (BH) adducts is reported. The protocol involves a nucleophilic substitution of the acetates of BH adducts with renewable natural alpha-amino esters followed by base-catalyzed intramolecular Michael addition. These sequential reactions are operationally simple, performed under ambient conditions, and give 81-93% yields of the target [1,4]oxazepin-2-ones. Thus, the present invention opens up a new aspect for the synthetic utility of BH adducts.

• 出版日期2009-4-1