Erratum: Palladium-catalyzed chemo- and enantioselective oxidation of allylic esters and carbonates (Journal of the American Chemical Society (2006) 128 (2540-2541) DOI: 10.1021/ja057163d)

Full text of DOI:10.1021/ja312194k

Addition/Correction
pubs.acs.org/JACS
Correction to “Palladium-Catalyzed Chemo- and Enantioselective
Oxidation of Allylic Esters and Carbonates”
Barry M. Trost,* Jeffery Richardson, and Kelvin Yong
J. Am. Chem. Soc. 2006, 128, 2540−2541. DOI: 10.1021/ja057163d
S
* Supporting Information
In the table of contents graphic and Supporting Information,
the absolute stereochemistry of the products for Table 2,
entries 1−3 (pages S17−S19) should be revised, based on
evaluation of the optical rotation data for the product in entry
2. The obtained rotation for this compound, [α]D = −179.6 (c
= 0.64, CHCl3), is of comparable magnitude but opposite sign
to the literature value for (R)-4-benzoyloxycyclohex-2-enone,
[α]20 = +201 (c = 0.85, CHCl3).1 Thus, the corrected
D
stereochemical assignment is (S)-4-benzoyloxycyclohex-2-
enone. This analysis was performed incorrectly in the
Supporting Information, and the incorrect structure was
drawn on page S17. By analogy, the structures for entries 1
and 3 in the Supporting Information should also be changed to
the (S) products. However, the correct structures are drawn in
the Communication itself (page 2541, Table 2, entries 1−3).
Notably, this corrected sense of stereoinduction is in line with
empirical models for π-allylpalladium reactions.2
ASSOCIATED CONTENT
* Supporting Information
Experimental procedures and characterization data for all new
compounds (corrected). This material is available free of charge
via the Internet at http://pubs.acs.org.
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REFERENCES
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(1) Yu, L.; Zhang, R.; Wang, Z. J. Chem. Soc., Perkin Trans. 1 2001,
2958.
(2) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
Published: February 22, 2013
© 2013 American Chemical Society
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