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Generation and electrophile trapping of N-Boc-2-lithio-2-azetine: synthesis of 2-substituted 2-azetines.

Abstract:
s-BuLi-induced α-lithiation-elimination of LiOMe from N-Boc-3-methoxyazetidine and further in situ α-lithiation generates N-Boc-2-lithio-2-azetine which can be trapped with electrophiles, either directly (carbonyl or heteroatom electrophiles) or after transmetalation to copper (allowing allylations and propargylations), providing a concise access to 2-substituted 2-azetines.
Publication status:
Published

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Publisher copy:
10.1021/ol403626k

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Pearson, CI More by this author
Journal:
Organic letters
Volume:
16
Issue:
3
Pages:
856-859
Publication date:
2014-02-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:11d917af-6dec-4931-8ddd-a6b9515619d1
Source identifiers:
446606
Local pid:
pubs:446606

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