Synthesis of Enantioenriched Vicinal Tertiary and Quaternary Carbon Stereogenic Centers within an Acyclic Chain

被引:112
作者
Pierrot, David [1 ]
Marek, Ilan [1 ]
机构
[1] Technion Israel Inst Technol, Schulich Fac Chem, Mallat Family Lab Organ Chem, IL-3200009 Haifa, Israel
基金
欧洲研究理事会;
关键词
diastereodivergence; quaternary stereogenic centers; stereogenic centers; tertiary stereogenic centers; vicinal positions; ASYMMETRIC ALLYLIC ALKYLATION; C-C BONDS; CATALYTIC ENANTIOSELECTIVE CONSTRUCTION; REMOTE FUNCTIONALIZATION; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; CLAISEN REARRANGEMENT; CONTIGUOUS QUATERNARY; CONJUGATE ADDITIONS; ADJACENT QUATERNARY; MICHAEL ADDITION;
D O I
10.1002/anie.201903188
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Overcoming the inherent difficulty to prepare quaternary carbon stereogenic centers, the diastereo- and enantioselective preparation of acyclic carbon backbones possessing vicinal quaternary and tertiary stereogenic centers (i.e. in a 1,2-relationship) causes distorted geometries and represents a very acute problem in organic synthesis. Several approaches are discussed in this minireview underlining the challenges illustrated by the rather limited number of approaches available to practitioners.
引用
收藏
页码:36 / 49
页数:14
相关论文
共 93 条
[1]   Total Synthesis of Pinnatoxins A and G and Revision of the Mode of Action of Pinnatoxin A [J].
Araoz, Romulo ;
Servent, Denis ;
Molgo, Jordi ;
Iorga, Bogdan I. ;
Fruchart-Gaillard, Carole ;
Benoit, Evelyne ;
Gu, Zhenhua ;
Stivala, Craig ;
Zakarian, Armen .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (27) :10499-10511
[2]   Congested C-C Bonds by Pd-Catalyzed Enantioselective Allyl-Allyl Cross-Coupling, a Mechanism-Guided Solution [J].
Ardolino, Michael J. ;
Morken, James P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (19) :7092-7100
[3]   Organocatalytic Formation of Quaternary Stereocenters [J].
Bella, Marco ;
Gasperi, Tecla .
SYNTHESIS-STUTTGART, 2009, (10) :1583-1614
[4]   BIOMIMETIC CONTROL OF CHEMICAL SELECTIVITY [J].
BRESLOW, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1980, 13 (06) :170-177
[5]   Efficient and stereodivergent synthesis of unsaturated acyclic fragments bearing contiguous stereogenic elements [J].
Bruffaerts, Jeffrey ;
Pierrot, David ;
Marek, Ilan .
NATURE CHEMISTRY, 2018, 10 (11) :1164-1170
[6]   Facile Construction of Vicinal Quaternary and Tertiary Stereocenters via Regio- and Stereoselective Organocatalytic Michael Addition to Nitrodienes [J].
Chauhan, Pankaj ;
Chimni, Swapandeep Singh .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (17) :3203-3212
[7]   Stereoselective construction of quaternary stereocenters [J].
Christoffers, J ;
Baro, A .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1473-1482
[8]  
Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO
[9]  
2-V
[10]  
Christoffers J., 2001, Angew. Chem, V113, P4725, DOI [10.1002/1521-3757(20011217)113:24, DOI 10.1002/1521-3757(20011217)113:24]