A New Type of Stereoselectivity in Baeyer–Villiger Reactions: Access to E- and Z-Olefins
recorded in ESI and APCI mode were performed on a Ther-
moScientific LTQ-FT spectrometer. Conversion and diaste-
reoisomeric composition were determined by achiral gas
chromatography as described. Alternatively, product 4b dia-
stereomeric mixture was determined by HPLC. Diastereo-
isomeric assignments were determined as described in the
Supporting Information. Analytical thin layer chromatogra-
phy was performed on Merck silica gel 60 F254q while for
column chromatography Merck silica gel 60 (230–400 mesh
ASTM) was used. Reactions that required inert atmosphere
(nitrogen or argon) were carried out using standard Schlenk
techniques. GC analyses were performed on a HP 6890
series while HPLC data were measured on a Shimadzu LC-
8 A. Crystallographic data for the structure of E-4b has
been deposited with the Cambridge Crystallographic Data
Centre (CCDC 880686). These data can be obtained free of
charge from The Cambridge Crystallographic Data Centre
CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. [fax:
+44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk].
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We thank Stephanie Dehn for GC analyses, Heike Hinrichs
and Alfred Deege for HPLC analyses, and Dr. Richard God-
dard for the X-ray structure determination of lactone E-4b.
Financial support by the Max-Planck-Society and the Arthur
C. Cope Foundation is gratefully acknowledged.
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