Catalytic asymmetric aldol reactions. Use of a chiral (acyloxy)borane complex as a versatile Lewis-acid catalyst

1991 ◽  
Vol 113 (3) ◽  
pp. 1041-1042 ◽  
Author(s):  
Kyoji Furuta ◽  
Tohru Maruyama ◽  
Hisashi Yamamoto
Keyword(s):  
Lewis Acid ◽  
Acid Catalyst ◽  
Aldol Reactions ◽  
Asymmetric Aldol ◽  
Lewis Acid Catalyst ◽  
Catalytic Asymmetric

Catalytic asymmetric allylation using a chiral (acyloxy)borane complex as a versatile Lewis acid catalyst

1993 ◽  
Vol 115 (24) ◽  
pp. 11490-11495 ◽  
Author(s):  
Kazuaki Ishihara ◽  
Makoto Mouri ◽  
Qingzhi Gao ◽  
Tohru Maruyama ◽  
Kyoji Furuta ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Acid Catalyst ◽  
Asymmetric Allylation ◽  
Lewis Acid Catalyst ◽  
Catalytic Asymmetric

ChemInform Abstract: Catalytic Asymmetric Allylation Using a Chiral (Acyloxy)borane Complex as a Versatile Lewis Acid Catalyst.

ChemInform ◽  
2010 ◽  
Vol 25 (11) ◽  
pp. no-no
Author(s):  
K. ISHIHARA ◽  
M. MOURI ◽  
Q. GAO ◽  
T. MARUYAMA ◽  
K. FURUTA ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Acid Catalyst ◽  
Asymmetric Allylation ◽  
Lewis Acid Catalyst ◽  
Catalytic Asymmetric

scholarly journals Managing the retro-pathway in direct catalytic asymmetric aldol reactions of thioamides

2015 ◽  
Vol 6 (11) ◽  
pp. 6124-6132 ◽  
Author(s):  
Youmei Bao ◽  
Naoya Kumagai ◽  
Masakatsu Shibasaki
Keyword(s):  
Lewis Acid ◽  
Aldol Reactions ◽  
Asymmetric Aldol ◽  
Cooperative Catalysis ◽  
Brønsted Base ◽  
Catalytic Asymmetric

Thioamides are the preferred pronucleophiles for direct catalytic asymmetric aldol reactions in the context of soft Lewis acid/hard Brønsted base cooperative catalysis.

Computationally-Guided Investigation of Dual Amine/pi Lewis Acid Catalysts for Direct Additions of Aldehydes and Ketones to Unactivated Alkenes and Alkynes

2020 ◽  
Author(s):  
Eric Greve ◽  
Jacob D. Porter ◽  
Chris Dockendorff
Keyword(s):  
Lewis Acid ◽  
Density Functional ◽  
Acid Catalyst ◽  
Metal Catalyst ◽  
Catalyst Poisoning ◽  
Lewis Acid Catalysts ◽  
Metal Ligands ◽  
Aldehydes And Ketones ◽  
Lewis Acid Catalyst ◽  
Catalyst Systems

Dual amine/pi Lewis acid catalyst systems have been reported for intramolecular direct additions of aldehydes/ketones to unactivated alkynes and occasionally alkenes, but related intermolecular reactions are rare and not presently of significant synthetic utility, likely due to undesired coordination of enamine intermediates to the metal catalyst. We reasoned that bulky metal ligands and bulky amine catalysts could minimize catalyst poisoning and could facilitate certain examples of direct intermolecular additions of aldehyde/ketones to alkenes/alkynes. Density Functional Theory (DFT) calculations were performed that suggested that PyBOX-Pt(II) catalysts for alkene/alkyne activation could be combined with MacMillan’s imidazolidinone organocatalyst for aldehyde/ketone activation to facilitate desirable C-C bond formations, and certain reactions were calculated to be more exergonic than catalyst poisoning pathways. As calculated, preformed enamines generated from the MacMillan imidazolidinone did not displace ethylene from a biscationic (<i>t</i>-Bu)PyBOX-Pt<sup>2+</sup>complex, but neither were the desired C-C bond formations observed under several different conditions.

Computationally-Guided Investigation of Dual Amine/pi Lewis Acid Catalysts for Direct Additions of Aldehydes and Ketones to Unactivated Alkenes and Alkynes

2020 ◽  
Author(s):  
Eric Greve ◽  
Jacob D. Porter ◽  
Chris Dockendorff
Keyword(s):  
Lewis Acid ◽  
Density Functional ◽  
Acid Catalyst ◽  
Metal Catalyst ◽  
Catalyst Poisoning ◽  
Lewis Acid Catalysts ◽  
Metal Ligands ◽  
Aldehydes And Ketones ◽  
Lewis Acid Catalyst ◽  
Catalyst Systems

Dual amine/pi Lewis acid catalyst systems have been reported for intramolecular direct additions of aldehydes/ketones to unactivated alkynes and occasionally alkenes, but related intermolecular reactions are rare and not presently of significant synthetic utility, likely due to undesired coordination of enamine intermediates to the metal catalyst. We reasoned that bulky metal ligands and bulky amine catalysts could minimize catalyst poisoning and could facilitate certain examples of direct intermolecular additions of aldehyde/ketones to alkenes/alkynes. Density Functional Theory (DFT) calculations were performed that suggested that PyBOX-Pt(II) catalysts for alkene/alkyne activation could be combined with MacMillan’s imidazolidinone organocatalyst for aldehyde/ketone activation to facilitate desirable C-C bond formations, and certain reactions were calculated to be more exergonic than catalyst poisoning pathways. As calculated, preformed enamines generated from the MacMillan imidazolidinone did not displace ethylene from a biscationic (<i>t</i>-Bu)PyBOX-Pt<sup>2+</sup>complex, but neither were the desired C-C bond formations observed under several different conditions.

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