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Unexpected rearrangement of enantiomerically pure 3‐aminoquinuclidine as a simple way of preparing diastereomeric octahydropyrrolo[2,3‐c]pyridine derivatives
Author(s) -
Goljer Igor,
Molinari Albert,
He Yanan,
Nogle Lisa,
Sun Weilin,
Campbell Brandon,
McConnell Oliver
Publication year - 2009
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20663
Subject(s) - chemistry , diastereomer , pyridine , absolute configuration , circular dichroism , nuclear magnetic resonance spectroscopy , spectroscopy , stereochemistry , organic chemistry , physics , quantum mechanics
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. Chirality, 2009. © 2008 Wiley‐Liss, Inc.