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, 131 (48), 17548-9

A Convergent Stereoselective Synthesis of Quinolizidines and Indolizidines: Chemoselective Coupling of 2-hydroxymethyl-substituted Allylic Silanes With Imines

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A Convergent Stereoselective Synthesis of Quinolizidines and Indolizidines: Chemoselective Coupling of 2-hydroxymethyl-substituted Allylic Silanes With Imines

Dexi Yang et al. J Am Chem Soc.

Abstract

A convergent synthesis of stereodefined indolizidines and quinolizidines through chemoselective allyl transfer between 2-hydroxymethyl-substituted allylic silanes and imines is described. Overall, highly substituted heterocycles that contain three stereogenic centers and up to four fused rings can be accessed in two steps from relatively simple coupling partners.

Figures

Figure 1
Figure 1
Introduction to indolizidines and quinolizidines.
Figure 2
Figure 2
Indolizidine and quinolizidine synthesis by: 1) chemoselective allyltransfer, and 2) cationic annulation.
Figure 3
Figure 3
Synthesis of complex heterocycles.

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