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

共 41 条

[1] B-(gamma-(trimethylsilyl)propargyl)diisopinocampheylborane: A new, highly efficient reagent for the enantioselective propargylboration of aldehydes. Synthesis of trimethylsilyl-substituted and parent alpha-allenic alcohols in high optical purity
Brown, HC
Khire, UR
Narla, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (25) : 8130 - 8131
[2] Asymmetric allyl- and crotylboration with the robust, versatile, and recyclable 10-TMS-9-borabicyclo[3.3.2]decanes
Burgos, CH
Canales, E
Matos, K
Soderquist, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (22) : 8044 - 8049
[3] B-allyl-10-Ph-9-borabicyclo[3.3.2]decanes:: Strategically designed for the asymmetric allylboration of ketones
Canales, E
Prasad, KG
Soderquist, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) : 11572 - 11573
[4] Asymmetric synthesis of isomerically pure allenyl boranes from alkynyl boranes through a 1,2-insertion-1,3-borotropic rearrangement
Canales, Eda
Gonzalez, Ana Z.
Soderquist, John A.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (03) : 397 - 399
[5] Nonracemic 3°-carbamines from the asymmetric allylboration of N-trimethylsilyl ketimines with B-allyl-10-phenyl-9-borabicyclo[3.3.2]decanes
Canales, Eda
Hernandez, Eliud
Soderquist, John A.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (27) : 8712 - 8713
[6] Chen GM, 1999, ANGEW CHEM INT EDIT, V38, P825, DOI 10.1002/(SICI)1521-3773(19990315)38:6<825::AID-ANIE825>3.0.CO
[7] 2-V
[8] An efficient synthesis of N-unsubstituted imines as organoborane adducts stable at room temperature:: New promising intermediates for synthesis
Chen, GM
Brown, HC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) : 4217 - 4218
[9] Highly Diastereoselective and Enantiospecific Allylation of Ketones and Imines Using Borinic Esters: Contiguous Quaternary Stereogenic Centers
Chen, Jack L-Y.
Aggarwal, Varinder K.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (41) : 10992 - 10996
[10] Synthesis, enantioresolution, and activity profile of chiral 6-methyl-2,4-disubstituted pyridazin-3(2H)-ones as potent N-formyl peptide receptor agonists
Cilibrizzi, Agostino
Schepetkin, Igor A.
Bartolucci, Gianluca
Crocetti, Letizia
Dal Piaz, Vittorio
Giovannoni, Maria Paola
Graziano, Alessia
Kirpotina, Liliya N.
Quinn, Mark T.
Vergelli, Claudia
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (12) : 3781 - 3792

← 1 2 3 4 5 →