Synthesis of Functionalized Pyrrolidines by a Highly Stereoselective [3+2]-Annulation Reaction of N-Tosyl-α-Amino Aldehydes and 1,3-Bis(silyl)propenes

Abstract

An efficient protocol for stereoselective construction of densely functionalized pyrrolidines by a [3+2]-annulation reaction of N-tosyl-α-amino aldehydes and 1,3-bis(silyl)propenes is described. This methodology is also applied as a key step in the synthesis of the polyhydroxylated pyrrolidine alkaloid 2,5-dideoxy-2,5-imino-d-glucitol (DGDP).

Key words

α-amino aldehyde - allylsilane - [3+2] annulation - pyrrolidine - alkaloid

References

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15

Silane 3c was prepared by the same method as 3d.

21

The [3+2] annulation of (S)-2a and 3e afforded 1b with >97% ee according to chiral HPLC analysis (Chiracel OD-H, hexane-i-PrOH, 99:1, 1 mL/min).

27

The Z-silane 9 was obtained as a side product in the synthesis of silane 3e (see ref. 18).