TY - JOUR
T1 - Palladium-catalyzed, asymmetric Baeyer–Villiger oxidation of prochiral cyclobutanones with PHOX ligands
AU - Petersen, Kimberly S.
AU - Stoltz, Brian M.
N1 - KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): KUS-11-006-02
Acknowledgements: This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST).
This publication acknowledges KAUST support, but has no KAUST affiliated authors.
PY - 2011/6
Y1 - 2011/6
N2 - Described in this report is a general method for the conversion of prochiral 3-substituted cyclobutanones to enantioenriched γ-lactones through a palladium-catalyzed Baeyer-Villiger oxidation using phosphinooxazoline ligands in up to 99% yield and 81% ee. Lactones of enantiopurity ≥93% could be obtained through a single recrystallization step. Importantly, 3,3-disubtituted cyclobutanones produced enantioenriched lactones containing a β-quaternary center. © 2011 Elsevier Ltd. All rights reserved.
AB - Described in this report is a general method for the conversion of prochiral 3-substituted cyclobutanones to enantioenriched γ-lactones through a palladium-catalyzed Baeyer-Villiger oxidation using phosphinooxazoline ligands in up to 99% yield and 81% ee. Lactones of enantiopurity ≥93% could be obtained through a single recrystallization step. Importantly, 3,3-disubtituted cyclobutanones produced enantioenriched lactones containing a β-quaternary center. © 2011 Elsevier Ltd. All rights reserved.
UR - http://hdl.handle.net/10754/599133
UR - https://linkinghub.elsevier.com/retrieve/pii/S0040402011005539
UR - http://www.scopus.com/inward/record.url?scp=79957528640&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2011.04.046
DO - 10.1016/j.tet.2011.04.046
M3 - Article
SN - 0040-4020
VL - 67
SP - 4352
EP - 4357
JO - Tetrahedron
JF - Tetrahedron
IS - 24
ER -