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

被引：7

作者：

Alicea-Matias, Eyleen ^{[1
]}

Soderquist, John A. ^{[1
]}

机构：

[1] Univ Puerto Rico, Dept Chem, Rio Piedras, PR 00931 USA

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 02期

关键词：

HIGHLY SELECTIVE REAGENTS; ENANTIOSELECTIVE SYNTHESIS; TERTIARY-CARBINOLS; ALLYLBORATION; IMINES; KETONES; ROBUST; PROPARGYLATION; EFFICIENT; VERSATILE;

D O I：

10.1021/acs.orglett.6b03506

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Available in either enantiomerically pure form through quantitative Grignard procedures from air-stable crystalline complexes (1, 3), the B-gamma-TMS propargylic derivatives of the 10-TMS- (2) and 10-phenyl-9-borabi-cyclo[3.3.2]decanes (4) provide highly selective entries to 2 degrees-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.

引用

页码：336 / 339

页数：4

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