Dielectrophilic Allenic Ketone-Enabled [4 + 2] Annulation with 3,3’-Bisoxindoles: Enantioselective Creation of Two Contiguous Quaternary Stereogenic Centers

ACS Catalysis ◽  
2021 ◽  
Vol 11 (3) ◽  
pp. 1361-1367
Author(s):  
Xiaodong Tang ◽  
Chuan Xiang Alvin Tan ◽  
Wai-Lun Chan ◽  
Fuhao Zhang ◽  
Wenrui Zheng ◽  
...  
Keyword(s):  
Stereogenic Centers ◽  
Quaternary Stereogenic Centers

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.

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.

scholarly journals Optically Pure Aziridin-2-yl Methanols as Readily Available 1H NMR Sensors for Enantiodiscrimination of α-Racemic Carboxylic Acids Containing Tertiary or Quaternary Stereogenic Centers

2020 ◽  
Vol 85 (18) ◽  
pp. 11794-11801
Author(s):  
Martyna Malinowska ◽  
Szymon Jarzyński ◽  
Adam Pieczonka ◽  
Michał Rachwalski ◽  
Stanisław Leśniak ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
1H Nmr ◽  
Stereogenic Centers ◽  
Optically Pure ◽  
Quaternary Stereogenic Centers
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