A short diastereoselective synthesis of cis-(2S,4S) and cis-(2R,4R)-4-hydroxyprolines

作者：Gajare Vikas S; Khobare Sandip R; Malavika B; Rajana Nagaraju; Rao B Venkateswara; Kumar U K Syam^*

来源：Tetrahedron Letters, 2015, 56(24): 3743-3746.

DOI：10.1016/j.tetlet.2015.03.119

• Diastereoselective synthesis
• cis-4-Hydroxyproline
• Diastereoselective epoxide opening
• Six membered transition state
• Zinc and magnesium enolates

A concise synthesis of (2R,4R)-4-hydroxyproline (1) and (2,5,45)-4-hydroxyproline (2) has been developed in enantiomerically pure form from commercially available starting materials with excellent diastereoselectivity. The tightly bound chelation controlled transition state formed during the 5-exo-tet ring closure reaction is assumed to be the origin of high diastereoselectivity.

• 出版日期2015-6-10