Application of Crystallization-Induced Asymmetric Transformation to a General, Scalable Method for the Resolution of 2,8-Disubstituted Troger's Base Derivatives

被引：19

作者：

Jameson, Donald L. ^{[1
]}

Field, Thomas ^{[1
]}

Schmidt, Monica R. ^{[1
]}

DeStefano, Alyson K. ^{[1
]}

Stiteler, Christopher J. ^{[1
]}

Venditto, Vincent J. ^{[1
]}

Krovic, Brooke ^{[1
]}

Hoffman, Christopher M. ^{[1
]}

Ondisco, Matthew T. ^{[1
]}

Belowich, Matthew E. ^{[1
]}

机构：

[1] Gettysburg Coll, Dept Chem, Gettysburg, PA 17325 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 22期

关键词：

ABSOLUTE-CONFIGURATION; SUBSTITUTED ANALOGS; SEPARATIONS; CHEMISTRY;

D O I：

10.1021/jo401873x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method for the gram scale resolution of 2-substituted and 2,8-disubstituted Troger's base (TB) derivatives in 63-91% yield has been achieved through the application of crystallization-induced asymmetric transformation (CIAT). Enantiomeric ratios of the resolved TB derivatives range from 99.1:0.9 to >99.5:0.5. Among the Troger's base compounds resolved are four synthetically valuable bromo and iodo derivatives.

引用

页码：11590 / 11596

页数：7

共 3 条

[1] General protocols for the synthesis of C2-symmetric and asymmetric 2,8-disubstituted analogues of Troger's base via efficient bromine-lithium exchanges of 2,8-dibromo-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine
Jensen, J
Tejler, J
Wärnmark, K
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17): : 6008 - 6014
[2] First stereoselective synthesis of 2-deoxy-α-D-ribosyl-1-phosphate:: Novel application of crystallization-induced asymmetric transformation
Komatsu, H
Awano, H
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15): : 5419 - 5421
[3] Crystallization-induced asymmetric transformations.: Enantiomerically pure (-)-(R)- and (+)-(S)-2,3-dibromopropan-1-ol and epibromohydrins.: A study of dynamic resolution via the formation of diastereoisomeric esters
Brunetto, G
Gori, S
Fiaschi, R
Napolitano, E
HELVETICA CHIMICA ACTA, 2002, 85 (11) : 3785 - 3791

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