An Approach to 3-Oxa-7-azabicyclo[3.3.0]octanes – Bicyclic Morpholine Surrogates

Abstract

An approach to 3-oxa-7-azabicyclo[3.3.0]octanes, bicyclic morpholine analogues, is reported, which relies on [3+2] cycloaddition of maleic anhydrides or furan-2(5H)-ones and an in situ generated azomethine ylide. The utility of the method was demonstrated on a multigram scale.

Selective [3 + 2] cycloaddition reaction of isothiazol‐3(2h)‐ones with in situ formed azomethine ylide to thiazolidines and oxazolidines

“…Recently, the [3 + 2] cycloaddition reaction of cyclic α, β-unsaturated carbonyl compounds with the nonstabilized azomethine has witnessed rapid development and drawn much attention [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18]. Pyrrolidines and oxazolidines could be obtained via the [3 + 2] cycloaddition reaction (Scheme 1) [19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35]. This concise method allowed rapid access to a number of thiazolidines and pyrrolidines derivatives in good yields with excellent Wen Bin Jin and Zhen Wang contributed equally to this study.…”