Chiral Amino Alcohol Accelerated and Stereocontrolled Allylboration of Iminoisatins: Highly Efficient Construction of Adjacent Quaternary Stereogenic Centers

2017 ◽  
Vol 56 (17) ◽  
pp. 4829-4833 ◽  
Author(s):  
Qiuyuan Tan ◽  
Xinqiao Wang ◽  
Yang Xiong ◽  
Zimeng Zhao ◽  
Lu Li ◽  
...  
Keyword(s):  
Amino Alcohol ◽  
Highly Efficient ◽  
Stereogenic Centers ◽  
Efficient Construction ◽  
Quaternary Stereogenic Centers

scholarly journals NHC-Catalyzed Organocatalytic Asymmetric Approach to 2,2-Disubstituted Benzofuran-3(2H)-ones Containing Fully Substituted Quaternary Stereogenic Center

Catalysts ◽  
2019 ◽  
Vol 9 (2) ◽  
pp. 192 ◽  
Author(s):  
Zbigniew Rafiński
Keyword(s):  
Stetter Reaction ◽  
Highly Efficient ◽  
Stereogenic Centers ◽  
Michael Acceptors ◽  
High Yields ◽  
Stereogenic Center ◽  
Quaternary Stereogenic Centers ◽  
Triazolium Salts

A highly efficient and enantioselective approach to the synthesis of functionalized benzofuran-3(2H)-ones is presented. It proceeds via an intramolecular Stetter reaction using β,β-disubstituted Michael acceptors in the construction of five-membered rings with fully-substituted quaternary stereogenic centers and is promoted by terpene-derived triazolium salts. As a result, a series of chiral 2,2-disubstituted benzofuran-3(2H)-one derivatives with linear, branched, and cyclic aliphatic substitutions on the quaternary stereogenic center were obtained in high yields and with excellent enantioselectivities of up to 99% ee.

Convergent Asymmetric Synthesis of a Renin Inhibitor: A Highly Efficient Construction Method of Three Stereogenic Centers

2013 ◽  
Vol 17 (11) ◽  
pp. 1430-1439 ◽  
Author(s):  
Makoto Michida ◽  
Yoshihiro Takayanagi ◽  
Makoto Imai ◽  
Yukito Furuya ◽  
Kenichi Kimura ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Construction Method ◽  
Renin Inhibitor ◽  
Highly Efficient ◽  
Stereogenic Centers ◽  
Efficient Construction

Highly enantioselective synthesis of bisoxindoles with two vicinal quaternary stereocenters via Lewis base mediated addition of oxindoles to isatin-derived ketimines

2014 ◽  
Vol 12 (32) ◽  
pp. 6085-6088 ◽  
Author(s):  
Zhongkai Tang ◽  
Yan Shi ◽  
Haibin Mao ◽  
Xuebin Zhu ◽  
Weipeng Li ◽  
...  
Keyword(s):  
Efficient Method ◽  
Enantioselective Synthesis ◽  
Lewis Base ◽  
Highly Efficient ◽  
Stereogenic Centers ◽  
Quaternary Stereocenters ◽  
Quaternary Stereogenic Centers

A highly efficient method provides access to the bisoxindole structure moiety with two vicinal quaternary stereogenic centers (>99 : 1 dr, >99% ee).

All-Carbon Quaternary Stereogenic Centers in Acyclic Systems through the Creation of Several C–C Bonds per Chemical Step

2014 ◽  
Vol 136 (7) ◽  
pp. 2682-2694 ◽  
Author(s):  
Ilan Marek ◽  
Yury Minko ◽  
Morgane Pasco ◽  
Tom Mejuch ◽  
Noga Gilboa ◽  
...  
Keyword(s):  
Stereogenic Centers ◽  
The Creation ◽  
Quaternary Stereogenic Centers

Chirality Transfer from a Chiral Primary Alcohol Equivalent Through Allyl Cyanate-to-Isocyanate Rearrangement: Synthesis of (+)-Geranyllinaloisocyanide

Synthesis ◽  
2019 ◽  
Vol 51 (15) ◽  
pp. 2959-2964 ◽  
Author(s):  
Yoshiyasu Ichikawa ◽  
Hirofumi Morimoto ◽  
Toshiya Masuda
Keyword(s):  
Natural Product ◽  
Primary Alcohol ◽  
Marine Natural Product ◽  
Chirality Transfer ◽  
New Approach ◽  
Stereogenic Centers ◽  
Quaternary Stereogenic Centers

A new approach was developed to construct quaternary stereogenic centers bearing nitrogen substituents in an enantioselective manner. The strategy takes advantage of [1,3]-chirality transfer from a chiral primary alcohol equivalent through an allyl cyanate-to-isocyanate rearrangement. This approach was employed in an efficient eight-step synthesis of the marine natural product, (+)-geranyllinaloisocyanide, in 43% overall yield.

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