Unexpected rearrangement of enantiomerically pure 3-aminoquinuclidine as a simple way of preparing diastereomeric octahydropyrrolo[2,3-c]pyridine derivatives.

Abstract:

:Reaction of (S)- or (R)-3-aminoquinuclidine with 2-chloropyrimidine or 2-bromopyrimidine led to an unexpected formation of both cis- and trans-octahydropyrrolo [2,3]pyridine derivatives. A single-step synthesis of two of the four stereoisomers of these octahydropyrrolo[2,3]pyridine derivatives provides a convenient way of generating stereochemically defined isomers. Optimization of reaction conditions was carried out by (1)H NMR monitoring. The relative and absolute stereochemistry of all four stereoisomers was determined by a combination of (1)H, (13)C, and (15)N NMR spectroscopy and vibrational circular dichroism spectroscopy.

journal_name

Chirality

journal_title

Chirality

authors

Goljer I,Molinari A,He Y,Nogle L,Sun W,Campbell B,McConnell O

doi

10.1002/chir.20663

subject

Has Abstract

pub_date

2009-07-01 00:00:00

pages

681-91

issue

7

eissn

0899-0042

issn

1520-636X

journal_volume

21

pub_type

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