A New Approach to Allylamines and Pyrrolidines | Zendy

Gajda Tadeusz | Zendy; Zwierzak Andrzej | Zendy

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A New Approach to Allylamines and Pyrrolidines

Author(s) -

Gajda Tadeusz,

Zwierzak Andrzej

Publication year - 1986

Publication title -

liebigs annalen der chemie

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0170-2041

DOI - 10.1002/jlac.198619860604

Subject(s) - chemistry , adduct , pyrrole , transformation (genetics) , stereochemistry , organic chemistry , combinatorial chemistry , medicinal chemistry , biochemistry , gene

The 1,4‐adducts 3a – c and 4 , readily available from the reaction between diethyl N,N ‐dichlorophosphoramidate ( 1 ) and 1,3‐dienes, were found to be convenient precursors for the efficient synthesis of the δ‐chloroallylamine hydrochlorides 5a – d and N ‐phosphorylated allylamines 6a – c and 7 . The three‐step transformation of 3a – c affords the cis ‐3,4‐dibromopyrrolidine hydrochlorides 10a – c . The preparation of the 2,5‐dihydro‐1 H ‐pyrrole hydrochlorides 11a – c and trans ‐3,4‐dibromopyrrolidine hydrochlorides 13a – c is also described. The stereochemistry of the reaction is studied.

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