Synthesis 2013; 45(10): 1364-1372
DOI: 10.1055/s-0032-1316848
paper
© Georg Thieme Verlag Stuttgart · New York

Using the 9-BBN Group as a Transient Protective Group for the Functionalization of Reactive Chains of α-Amino Acids

Adrián Sánchez*
a   Departamento de Química Orgánica, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510, México D.F., México   Fax: +52(56)223722   eMail: ausbir@yahoo.com.mx   eMail: joseavm@unam.mx
,
Ernesto Calderón
b   Laboratorio de Inmunoquímica Hospital Infantil de México Federico Gómez, Dr. Márquez 162, Col Doctores, Cuauhtémoc, 06720, México D.F., Mexico
,
Alfredo Vazquez*
a   Departamento de Química Orgánica, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510, México D.F., México   Fax: +52(56)223722   eMail: ausbir@yahoo.com.mx   eMail: joseavm@unam.mx
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Publikationsverlauf

Received: 11. Dezember 2012

Accepted after revision: 01. Januar 2013

Publikationsdatum:
25. April 2013 (online)


Abstract

Achieving chemoselectivity is a longstanding challenge in chemical synthesis. This problem has been addressed using different approaches, but a definitive solution is still pending. For instance, in peptide chemistry, particularly with amino acids containing side chains functionalities with reactivity patterns similar to the main functional groups, such as aspartic and glutamic acids­, and lysine and ornithine, specific semi-permanent protecting groups have been employed. The use of 9-borabicyclo[3.3.1]nonane (9-BBN-H) as a transient protective group for the selective protection of α-amino acids, which allows the chemoselective manipulation of the functional groups embedded in the side chains of the molecule, is described.

Supporting Information