An asymmetric substrate-controlled Morita-Baylis-Hillman reaction as approach for the synthesis of pyrrolizidinones and pyrrolizidines

作者：Luna Freire Kristerson R; Scaramal Joao Paulo S; Resende Jackson A L C; Tormena Claudio F; Oliveira Fabio L; Aparicio Ricardo; Coelho Fernando^*

来源：Tetrahedron, 2014, 70(20): 3319-3326.

DOI：10.1016/j.tet.2013.10.050

• Morita-Baylis-Hillman
• Heterocycles
• Pyrrolizidines
• Heck reaction
• Stereoselectivity
• Absolute configuration

We describe herein an approach to the total synthesis of functionalized pyrrolizidinones and pyrrolizidines. The synthetic sequence is based on a highly stereoselective substrate-controlled Morita-Baylis-Hillman (MBH) reaction between a chiral amino-aldehyde and methyl acrylate. The selectivity attained in this reaction was controlled by the presence of a hydroxyl group adequately placed in the structure of the amino-aldehyde used as the nucleophilic component of the MBH reaction. The MBH adducts were used as substrate for an efficient total synthesis of pyrrolizidinones and pyrrolizidines in good overall yield.

• 出版日期2014-5-20