학술논문

A Convenient Method for 3-Pyrroline Synthesis

Document Type

Article

Author

Green, M. P.; Prodger, J. C.; Sherlock, A. E.; Hayes, C. J.

Source

Organic Letters; October 2001, Vol. 3 Issue: 21 p3377-3379, 3p

Subject

Language

ISSN

15237060; 15237052

Abstract

The synthesis of a range of 3-pyrrolines has been achieved from primary amine starting materials using a two-step alkylation/alkylidene carbene CH-insertion reaction sequence. We have shown that insertion into a range of CH-bond types is possible, and the formation of nitrogen-bearing quaternary stereocenters is a relatively facile process. The insertion reaction occurs with >95% retention of stereochemistry, but the presence of protecting groups on nitrogen is generally deleterious to the cyclization process.

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