Highly Diastereoselective Synthesis of Syn ‐1,3‐Dihydroxyketone Motifs from Propargylic Alcohols via Spiroepoxide Intermediates

2019 ◽  
Vol 131 (34) ◽  
pp. 11956-11961
Author(s):  
Xiao‐Bo Ding ◽  
Daniel P. Furkert ◽  
Margaret A. Brimble
Keyword(s):  
Diastereoselective Synthesis ◽  
Propargylic Alcohols

Indium(iii) chloride catalyzed highly diastereoselective domino synthesis of indenodithiepines and indenodithiocines

2015 ◽  
Vol 51 (4) ◽  
pp. 707-710 ◽  
Author(s):  
Sengodagounder Muthusamy ◽  
Manickasamy Sivaguru ◽  
Eringathodi Suresh
Keyword(s):  
Domino Reaction ◽  
Diastereoselective Synthesis ◽  
Propargylic Alcohols

An atom-economical diastereoselective synthesis of indenodithiepines and indenodithiocines has been developed via a domino reaction of propargylic alcohols and dithioacetals in the presence of InCl3 as a catalyst.

Copper-catalysed synthesis of α-alkylidene cyclic carbonates from propargylic alcohols and CO2

2021 ◽  
Author(s):  
Alejandro Cervantes-Reyes ◽  
Kaveh Farshadfar ◽  
Matthias Rudolph ◽  
Frank Rominger ◽  
Thomas Schaub ◽  
...  
Keyword(s):  
Chemical Fixation ◽  
Cyclic Carbonates ◽  
Diastereoselective Synthesis ◽  
Propargylic Alcohols ◽  
Effective Catalyst

A sterically encumbered, nine-membered NHC-copper(i) complex was shown to be an effective catalyst for the chemical fixation of CO2 by propargylic alcohols for the diastereoselective synthesis of α-alkylidene cyclic carbonates.

Remote C(sp3)–H vinylation via radical-mediated consecutive fission of C–H and C–C bonds

2020 ◽  
Vol 7 (19) ◽  
pp. 2981-2985
Author(s):  
Tao Niu ◽  
Shan Yang ◽  
Xinxin Wu ◽  
Chen Zhu
Keyword(s):  
Propargylic Alcohols

Described herein is a radical-mediated vinylation of the remote C(sp3)–H bonds of propargylic alcohols.

Gold Catalyzed Hydroamination of Propargylic Alcohols: Controlling Divergent Reaction Pathways to Access 1,3-Aminoalcohols, 3-Hydroxyketones or 3-Aminoketones

2018 ◽  
Author(s):  
Victor Laserna ◽  
Tom Sheppard
Keyword(s):  
Gold Catalysis ◽  
Reaction Pathways ◽  
High Yield ◽  
Reaction Conditions ◽  
Propargylic Alcohols ◽  
Catalytic Quantity ◽  
Selective Formation ◽  
General Method

A versatile approach to the valorization of propargylic alcohols is reported, enabling controlled access to three different products from the same starting materials. Firstly, a general method for the hydroamination of propargylic alcohols with anilines is described using gold catalysis to give 3-hydroxy imines with complete regioselectivity. These 3-hydroxyimines can be reduced to give 1,3-aminoalcohols with high syn seletivity. Alternatively, by using a catalytic quantity of aniline, 3-hydroxyketones can be obtained in high yield directly from propargylic alcohols. Further manipulation of the reaction conditions enables the selective formation of 3-aminoketones via a rearrangement/hydroamination pathway.<br>

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