Diastereoselective Rh-catalyzed decarboxylative allylation to form quaternary stereocenters using sulfinimine as the directing group

2019 ◽  
Vol 6 (6) ◽  
pp. 732-735 ◽  
Author(s):  
Shuanglin Qin ◽  
Tongtong Liu ◽  
Yunhao Luo ◽  
Shende Jiang ◽  
Guang Yang
Keyword(s):  
Directing Group ◽  
Quaternary Stereocenters ◽  
Decarboxylative Allylation ◽  
First Time

In this paper, we reported for the first time that the diastereoselective Rh-catalyzed decarboxylative allylation of chiral sulfinimines could be used to form quaternary stereocenters.

Diastereoselective Pd-catalyzed decarboxylative allylation to construct quaternary stereocenters using sulfinimine as the directing group

Synlett ◽  
2021 ◽  
Author(s):  
Sheng Cao ◽  
Chen Li ◽  
Xuan Wang ◽  
Yilei Huang ◽  
Guang Yang ◽  
...  
Keyword(s):  
Allylic Alkylation ◽  
Efficient Route ◽  
Directing Group ◽  
Chiral Centers ◽  
Quaternary Stereocenters ◽  
Decarboxylative Allylation ◽  
High Yields

A robust Pd(0)-catalyzed decarboxylation of allylic alkylation has been developed to construct quaternary stereocenters through the use of chiral tert-butanesulfinamide as the directing group. This strategy provides a simple and efficient route to the construction of quaternary chiral centers at the α-position of chiral sulfinamides, with high diastereoselectivities and high yields.

Pd-Catalyzed directedCH-(hetero)arylation of cyclic α-amino acids: effects of substituents and the ring size

2019 ◽  
Vol 17 (17) ◽  
pp. 4342-4349 ◽  
Author(s):  
Valeriia Hutskalova ◽  
Pavel K. Mykhailiuk
Keyword(s):  
Amino Acids ◽  
Systematic Study ◽  
Ring Size ◽  
Directing Group ◽  
First Time ◽  
Cyclic Amino Acids

A systematic study on the directed Pd-catalyzed (hetero)arylation of 26 substituted cyclic α-amino acids at the C(3)-atom was performed. For the first time, the 7- and 8-membered cyclic amino acids were introduced to C–H activation. 8–Aminoquinoline was used as a directing group.

Deracemization of Quaternary Stereocenters by Pd-Catalyzed Enantioconvergent Decarboxylative Allylation of Racemic β-Ketoesters

2005 ◽  
Vol 117 (42) ◽  
pp. 7084-7087 ◽  
Author(s):  
Justin T. Mohr ◽  
Douglas C. Behenna ◽  
Andrew M. Harned ◽  
Brian M. Stoltz
Keyword(s):  
Quaternary Stereocenters ◽  
Decarboxylative Allylation

scholarly journals Stereospecific, Ligand-Free Synthesis of All-Carbon Quaternary Stereocenters from Tertiary Benzylic Carboxylates

2021 ◽  
Author(s):  
Jianyu Xu ◽  
Sarah Pound ◽  
Corey Basch ◽  
Alana Duke ◽  
Mary Watson
Keyword(s):  
The Past ◽  
Ligand Free ◽  
Quaternary Stereocenters ◽  
High Yields ◽  
First Time

Nickel-catalyzed, stereospecific cross-couplings via activation of secondary C–O bonds has been well developed in the past few years. Meanwhile, stereospecific cross-couplings of tertiary electrophiles have been rarely explored. Herein, we describe a nickel-catalyzed, ligand-free Suzuki-Miyaura vinylation, using easily prepared, highly enantioenriched tertiary benzylic carboxylates to install all-carbon quaternary stereocenters in high yields and ee’s. In addition to allowing stereospecific vinylation of these substrates for the first time, this method overcomes the longstanding requirement for a naphthyl group on the benzylic carboxylate<br>

Deracemization of Quaternary Stereocenters by Pd-Catalyzed Enantioconvergent Decarboxylative Allylation of Racemic β-Ketoesters

2005 ◽  
Vol 44 (42) ◽  
pp. 6924-6927 ◽  
Author(s):  
Justin T. Mohr ◽  
Douglas C. Behenna ◽  
Andrew M. Harned ◽  
Brian M. Stoltz
Keyword(s):  
Quaternary Stereocenters ◽  
Decarboxylative Allylation

scholarly journals A dual role for acetohydrazide in Pd-catalyzed controlled C(sp3)–H acetoxylation of aldehydes

RSC Advances ◽  
2020 ◽  
Vol 10 (21) ◽  
pp. 12192-12196
Author(s):  
Juan Chen ◽  
Chaolumen Bai ◽  
XingWen Tong ◽  
Dan Liu ◽  
Yong-Sheng Bao
Keyword(s):  
Dual Role ◽  
Group Approach ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
First Time

The palladium catalyzed aldehyde directed acetoxylation of C(sp3)–H bonds was realized by a transient directing group approach for the first time.

Kinetic resolution of 2,2-disubstituted-1,3-diketones via carbene catalysis

2019 ◽  
Vol 6 (3) ◽  
pp. 290-298 ◽  
Author(s):  
Weici Xu ◽  
Yuanzhen Li ◽  
Rui Liu ◽  
Shuang Yang ◽  
Jian Liu ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Quaternary Stereocenters ◽  
First Time

Organocatalytic kinetic resolution of 1,3-diketones with central quaternary stereocenters was achieved for the first time. The resolution proceeds via two basic modes, and the inherent principles between the different combinations of ketone groups and the resolution patterns were also disclosed.

scholarly journals Directed C(sp3)–H arylation of tryptophan: transformation of the directing group into an activated amide

2019 ◽  
Vol 10 (37) ◽  
pp. 8634-8641 ◽  
Author(s):  
Lennart Nicke ◽  
Philip Horx ◽  
Klaus Harms ◽  
Armin Geyer
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Directing Group ◽  
First Time

The aminoquinoline-directed C–H activation was used to synthezise unnatural tryptophans for solid phase peptide synthesis for the first time.

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