Enantioselective Formation of All-Carbon Quaternary Stereocenters from Indoles and Tertiary Alcohols Bearing A Directing Group

2014 ◽  
Vol 54 (6) ◽  
pp. 1910-1913 ◽  
Author(s):  
Wanxiang Zhao ◽  
Zhaobin Wang ◽  
Boyang Chu ◽  
Jianwei Sun
Keyword(s):  
Tertiary Alcohols ◽  
Directing Group ◽  
Quaternary Stereocenters

Enantioselective Formation of All-Carbon Quaternary Stereocenters from Indoles and Tertiary Alcohols Bearing A Directing Group

2014 ◽  
Vol 127 (6) ◽  
pp. 1930-1933 ◽  
Author(s):  
Wanxiang Zhao ◽  
Zhaobin Wang ◽  
Boyang Chu ◽  
Jianwei Sun
Keyword(s):  
Tertiary Alcohols ◽  
Directing Group ◽  
Quaternary Stereocenters

Oxidation of chiral α-phenylacetate derivatives: formation of dimers with contiguous quaternary stereocenters versus tertiary alcohols

2005 ◽  
Vol 16 (21) ◽  
pp. 3599-3605 ◽  
Author(s):  
Marisa C. Kozlowski ◽  
Evan S. DiVirgilio ◽  
Krishnan Malolanarasimhan ◽  
Carol A. Mulrooney
Keyword(s):  
Tertiary Alcohols ◽  
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.

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.

para-Selective Cyanation of Arenes by H-Bonded Template

2019 ◽  
Author(s):  
Sandeep Pimparkar ◽  
Trisha Bhattacharya ◽  
Arun Maji ◽  
Argha Saha ◽  
Ramasamy Jayarajan ◽  
...  
Keyword(s):  
Selective Functionalization ◽  
Directing Group ◽  
Product Utility ◽  
Site Selective

The significance of site selective functionalization stands upon the superior selectivity, easy synthesis and diverse product utility. In this work we demonstrate the <i>para</i>-selective introduction of versatile nitrile moiety, enabled by detachable and reusable H-bonded auxiliary. The methodology holds its efficiency irrespective of substrate electronic bias. The conspicuous shift in the step energetics was probed by both experimental and computational mechanistic tools heralds the inception of <i>para</i>-deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications

para-Selective Cyanation of Arenes by H-Bonded Template

2019 ◽  
Author(s):  
Sandeep Pimparkar ◽  
Trisha Bhattacharya ◽  
Arun Maji ◽  
Argha Saha ◽  
Ramasamy Jayarajan ◽  
...  
Keyword(s):  
Selective Functionalization ◽  
Directing Group ◽  
Product Utility ◽  
Site Selective

The significance of site selective functionalization stands upon the superior selectivity, easy synthesis and diverse product utility. In this work we demonstrate the <i>para</i>-selective introduction of versatile nitrile moiety, enabled by detachable and reusable H-bonded auxiliary. The methodology holds its efficiency irrespective of substrate electronic bias. The conspicuous shift in the step energetics was probed by both experimental and computational mechanistic tools heralds the inception of <i>para</i>-deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications

Imine as a Linchpin Approach for Distal C(sp2)–H Functionalization

2020 ◽  
Author(s):  
Sukdev Bag ◽  
Sadhan Jana ◽  
Sukumar Pradhan ◽  
Suman Bhowmick ◽  
Nupur Goswami ◽  
...  
Keyword(s):  
Organic Molecules ◽  
Bond Activation ◽  
Bond Formation ◽  
Ancillary Ligand ◽  
Significant Challenge ◽  
Site Selectivity ◽  
Directing Group ◽  
Covalently Linked ◽  
Complex Organic ◽  
Post Functionalization

<p>Despite the widespread applications of C–H functionalization, controlling site selectivity remains a significant challenge. Covalently attached directing group (DG) served as an ancillary ligand to ensure proximal <i>ortho</i>-, distal <i>meta</i>- and <i>para</i>-C-H functionalization over the last two decades. These covalently linked DGs necessitate two extra steps for a single C–H functionalization: introduction of DG prior to C–H activation and removal of DG post-functionalization. We introduce here a transient directing group for distal C(<i>sp<sup>2</sup></i>)-H functionalization <i>via</i> reversible imine formation. By overruling facile proximal C-H bond activation by imine-<i>N</i> atom, a suitably designed pyrimidine-based transient directing group (TDG) successfully delivered selective distal C-C bond formation. Application of this transient directing group strategy for streamlining the synthesis of complex organic molecules without any necessary pre-functionalization at the distal position has been explored.</p>

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