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
Chiralityjournal_title
Chiralityauthors
Goljer I,Molinari A,He Y,Nogle L,Sun W,Campbell B,McConnell Odoi
10.1002/chir.20663subject
Has Abstractpub_date
2009-07-01 00:00:00pages
681-91issue
7eissn
0899-0042issn
1520-636Xjournal_volume
21pub_type
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