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Synthesis of 3-fluoropyrrolidines and 4-fluoropyrrolidin-2-ones from allylic fluorides.

Abstract:

Various 3-fluoropyrrolidines and 4-fluoropyrrolidin-2-ones were prepared by 5-exo-trig iodocyclisation from allylic fluorides bearing a pending nitrogen nucleophile. These bench-stable precursors were made accessible upon electrophilic fluorination of the corresponding allylsilanes. The presence of the allylic fluorine substituent induces syn-stereocontrol upon iodocyclisation with diastereomeric ratios ranging from 10:1 to > 20:1 for all N-tosyl-3-fluoropent-4-en-1-amines and amides. The ...

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Publication status:
Published

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Publisher copy:
10.1002/chem.201201576

Authors


Journal:
Chemistry (Weinheim an der Bergstrasse, Germany) More from this journal
Volume:
18
Issue:
41
Pages:
13126-13132
Publication date:
2012-10-01
DOI:
EISSN:
1521-3765
ISSN:
0947-6539
Language:
English
Keywords:
Pubs id:
pubs:352426
UUID:
uuid:078b93c7-1042-43f7-8fe6-d362b043a302
Local pid:
pubs:352426
Source identifiers:
352426
Deposit date:
2012-12-19

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