Synlett 2015; 26(06): 765-770
DOI: 10.1055/s-0034-1380128
letter
© Georg Thieme Verlag Stuttgart · New York

Gold-Catalyzed, SN1-Type Reaction of Alcohols to Afford Ethers and Cbz-Protected Amines

Andrew R. S. Vinson
Keck Science Department, Claremont McKenna, Pitzer and Scripps Colleges, 925 N. Mills Avenue, Claremont, CA 91711, USA   eMail: awenzel@kecksci.claremont.edu
,
Victoria K. Davis
Keck Science Department, Claremont McKenna, Pitzer and Scripps Colleges, 925 N. Mills Avenue, Claremont, CA 91711, USA   eMail: awenzel@kecksci.claremont.edu
,
Arunamarie Arunasalam
Keck Science Department, Claremont McKenna, Pitzer and Scripps Colleges, 925 N. Mills Avenue, Claremont, CA 91711, USA   eMail: awenzel@kecksci.claremont.edu
,
Kate A. Jesse
Keck Science Department, Claremont McKenna, Pitzer and Scripps Colleges, 925 N. Mills Avenue, Claremont, CA 91711, USA   eMail: awenzel@kecksci.claremont.edu
,
Rachael E. Hamilton
Keck Science Department, Claremont McKenna, Pitzer and Scripps Colleges, 925 N. Mills Avenue, Claremont, CA 91711, USA   eMail: awenzel@kecksci.claremont.edu
,
Morgan A. Shattuck
Keck Science Department, Claremont McKenna, Pitzer and Scripps Colleges, 925 N. Mills Avenue, Claremont, CA 91711, USA   eMail: awenzel@kecksci.claremont.edu
,
Allison C. Hu
Keck Science Department, Claremont McKenna, Pitzer and Scripps Colleges, 925 N. Mills Avenue, Claremont, CA 91711, USA   eMail: awenzel@kecksci.claremont.edu
,
Robert G. Iafe
Keck Science Department, Claremont McKenna, Pitzer and Scripps Colleges, 925 N. Mills Avenue, Claremont, CA 91711, USA   eMail: awenzel@kecksci.claremont.edu
,
Anna G. Wenzel*
Keck Science Department, Claremont McKenna, Pitzer and Scripps Colleges, 925 N. Mills Avenue, Claremont, CA 91711, USA   eMail: awenzel@kecksci.claremont.edu
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Publikationsverlauf

Received: 13. Dezember 2014

Accepted after revision: 06. Januar 2015

Publikationsdatum:
09. Februar 2015 (online)


Abstract

The use of a gold-catalyzed, microwave protocol to activate alcohols through an intermolecular, SN1-type reaction to directly form unsymmetrical ethers and N-benzyloxy carbamate- (Cbz) protected amines is reported. Results have shown this reaction to be highly reproducible and tolerant of moisture, and moderate to high product yields (53–99%) were obtained. Significantly, the intermolecular catalytic amination of alcohols to directly afford Cbz-protected amines is heretofore unprecedented using gold catalysis.

Supporting Information