Journal article icon

Journal article

Amine Protection/α-Activation with the tert-Butoxythiocarbonyl Group: Application to Azetidine Lithiation-Electrophilic Substitution.

Abstract:
tert-Butoxythiocarbonyl (Botc), the long-neglected thiocarbonyl analogue of Boc, facilitates (unlike its alkoxycarbonyl cousin) α-lithiation and electrophile incorporation on N-Botc-azetidine. N,N,N',N'-endo,endo-Tetramethyl-2,5-diaminonorbornane proved optimal as a chiral ligand, generating adducts with er up to 92:8. Facile deprotection, under conditions that left the corresponding N-Boc systems intact, was achieved using either TFA or via thermolysis in ethanol.

Actions


Access Document


Publisher copy:
10.1021/ol503441d

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Publisher:
American Chemical Society
Journal:
Organic letters More from this journal
Volume:
17
Issue:
2
Pages:
330-333
Publication date:
2015-01-01
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
Language:
English
Pubs id:
pubs:500823
UUID:
uuid:8bcdb554-2864-4864-a8c1-29a05ae0e9b7
Local pid:
pubs:500823
Source identifiers:
500823
Deposit date:
2015-01-08

Terms of use


Views and Downloads






If you are the owner of this record, you can report an update to it here: Report update to this record

TO TOP