Asymmetric Propargylboration of Aldimines and Ketimines with the Borabicyclo[3.3.2]decanes: Novel Entries to Allenyl Carbinamines, Amino Acids, and Their &#945;-Methyl Counterparts.

Alicea-Matías, Eyleen; Soderquist, John A

Asymmetric Propargylboration of Aldimines and Ketimines with the Borabicyclo[3.3.2]decanes: Novel Entries to Allenyl Carbinamines, Amino Acids, and Their α-Methyl Counterparts.

Alicea-Matías, Eyleen; Soderquist, John A.

Afiliação

Alicea-Matías E; Department of Chemistry, University of Puerto Rico , Rio Piedras 00931-3346, Puerto Rico.
Soderquist JA; Department of Chemistry, University of Puerto Rico , Rio Piedras 00931-3346, Puerto Rico.

Org Lett ; 19(2): 336-339, 2017 01 20.

Article em En | MEDLINE | ID: mdl-28045535

RESUMO

Available in either enantiomerically pure form through quantitative Grignard procedures from air-stable crystalline complexes (1, 3), the B-Î³-TMS propargylic derivatives of the 10-TMS- (2) and 10-phenyl-9-borabicyclo[3.3.2]decanes (4) provide highly selective entries to 2°-allenyl carbinamines (8, 60-85%, 78-99% ee) and their 3° counterparts (13, 62-82%, 95-99% ee) through their additions to aldimines and ketimines, respectively. The absolute configurations of these amines were obtained from the known amino acid derivatives 16eR and 19dR through the ozonolysis of 8eR and 13dR and from the single-crystal X-ray structure of 14fR.

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Org Lett Assunto da revista: BIOQUIMICA Ano de publicação: 2017 Tipo de documento: Article País de afiliação: Porto Rico País de publicação: Estados Unidos

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