In this section
@article{Boddy:2019:10.1021/acs.orglett.9b00407,
author = {Boddy, AJ and Cordier, C and Goldberg, K and Madin, A and Spivey, AC and Bull, J},
doi = {10.1021/acs.orglett.9b00407},
journal = {Organic Letters},
pages = {1818--1822},
title = {Acid-mediated ring-expansion of 2,2-disubstituted azetidine carbamates to 6,6-disubstituted 1,3-oxazinan-2-ones},
url = {http://dx.doi.org/10.1021/acs.orglett.9b00407},
volume = {21},
year = {2019}
}
TY - JOUR
AB - The ring expansion of 2-ester-2-aryl-azetidine carbamates can be achieved using Brønsted acids to form 6,6-disubstituted 1,3-oxazinan-2-ones. The reaction is rapid at room temperature with Boc or Cbz derivatives, and proceeds with excellent yield (up to 96%) and broad substrate scope. Derivatives of drug compounds and natural products are incorporated. The combina-tion of this ring expansion in a 3-step N–H insertion/cyclization/expansion (NICE) sequence is applied to directly access medicinally relevant scaffolds from acyclic precursors.
AU - Boddy,AJ
AU - Cordier,C
AU - Goldberg,K
AU - Madin,A
AU - Spivey,AC
AU - Bull,J
DO - 10.1021/acs.orglett.9b00407
EP - 1822
PY - 2019///
SN - 1523-7052
SP - 1818
TI - Acid-mediated ring-expansion of 2,2-disubstituted azetidine carbamates to 6,6-disubstituted 1,3-oxazinan-2-ones
T2 - Organic Letters
UR - http://dx.doi.org/10.1021/acs.orglett.9b00407
UR - http://hdl.handle.net/10044/1/68110
VL - 21
ER -
Email: a.c.spivey@imperial.ac.uk
Skype: alan.spivey
Tel & Fax: +44 (0)20 75945841
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