Amines Bearing Tertiary Substituents by Tandem Enantioselective

Jan 31, 2013 - Pages 34–37. Owing to our misrepresentation of the relative configuration of compound S1 and the absolute configuration of compound S...
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ORGANIC LETTERS 2013 Vol. 15, No. 4 974–976

Additions and Corrections Volume 15, 2013

Michael Tait, Morgan Donnard, Alberto Minassi, Julien Lefranc, Beatrice Bechi, Giorgio Carbone, Peter O’Brien, and Jonathan Clayden* Amines Bearing Tertiary Substituents by Tandem Enantioselective Carbolithiation Rearrangement of Vinylureas Pages 34 37. Owing to our misrepresentation of the relative configuration of compound S1 and the absolute configuration of compound S2 in the Supporting Information, all chiral, enantiomerically enriched compounds in this paper have erroneously been represented as their enantiomers. As a result the following corrections should be made:

Scheme 2

Abstract/TOC graphic. The Abstract/TOC graphic below shows the corrected structures.

Page 36, first paragraph. The sentence should read, “Since both protonation and aryl migration are stereochemically retentive,16 and carbolithiation is syn selective,6 we deduce that ( )-sparteine leads to aryl migration to the Si face of the alkenyl group;the front face as drawn;of vinyl ureas 1.” Page 37, second paragraph. The sentence should read, “We assume that the reactions begin with an asymmetric carbolithiation, in which the diamine-complexed organolithium attacks one enantiotopic face of the alkene (Si for 4; Re for 5) to form a stereodefined organolithium under kinetic control.” Schemes 2 5 show the corrected structures.

Scheme 3

Org. Lett., Vol. 15, No. 4, 2013

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Scheme 4

Scheme 5

Supporting Information Available. The name and structure of compounds S1 and S2 have been changed from R to S at the relevant stereogenic center in the revised file (p S-4). This material is available free of charge via the Internet at http://pubs.acs.org. 10.1021/ol4002009 Published on Web 01/31/2013

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Org. Lett., Vol. 15, No. 4, 2013