Solvent- or Temperature-Controlled Diastereoselective Aldol Reaction of Methyl Phenylacetate

2012 ◽  
Vol 14 (17) ◽  
pp. 4346-4349 ◽  
Author(s):  
P. Veeraraghavan Ramachandran ◽  
Prem B. Chanda
Keyword(s):  
Aldol Reaction ◽  
Temperature Controlled ◽  
Methyl Phenylacetate

Temperature-controlled Mukaiyama aldol reaction of cyclododecanone (CDD) with aromatic aldehydes promoted by TMSCl via the (TMS)3Si intermediate generated in situ

2016 ◽  
Vol 40 (4) ◽  
pp. 3833-3842 ◽  
Author(s):  
Venkatesan Sathesh ◽  
Kulathu I. Sathiyanarayanan
Keyword(s):  
Aldol Reaction ◽  
Aromatic Aldehydes ◽  
Diastereoselective Synthesis ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol ◽  
Temperature Controlled ◽  
Sterically Hindered

A temperature controlled chemo-, regio- and diastereoselective synthesis of enones and Mukaiyama aldol reaction have been developed using sterically hindered CDD with organosilane as a catalyst.

Random media with temperature controlled connectivity

1992 ◽  
Vol 2 (5) ◽  
pp. 503-510 ◽  
Author(s):  
F. Carmona ◽  
E. Valot ◽  
L. Servant ◽  
M. Ricci
Keyword(s):  
Random Media ◽  
Temperature Controlled

An Alternate Energy-Conserved Pathway for the Morita-Baylis-Hillman (MBH) Reaction

2020 ◽  
Author(s):  
Veejendra Yadav
Keyword(s):  
Proton Transfer ◽  
Transition State ◽  
Lower Energy ◽  
Aldol Reaction ◽  
Membered Ring ◽  
Ammonium Ion ◽  
Alternate Energy ◽  
Ring Transition State ◽  
Mbh Reaction

An new overall lower energy pathway for the amine-catalysed Morita-Baylis-Hillman reaction is proposed from computations at the M06-2X/6-311++G(d,p) level. The pathway involves proton-transfer from the ammonium ion to the alkoxide formed from the aldol reaction through a seven-membered ring transition state (TS) structure followed by highly exothermic Hofmann<i> </i>elimination through a five-membered ring TS structure to form the product and also release the catalyst to carry on with the process all over again.

An Alternate Energy-Conserved Pathway for the Morita-Baylis-Hillman (MBH) Reaction

2020 ◽  
Author(s):  
Veejendra Yadav
Keyword(s):  
Proton Transfer ◽  
Transition State ◽  
Lower Energy ◽  
Aldol Reaction ◽  
Membered Ring ◽  
Ammonium Ion ◽  
Alternate Energy ◽  
Ring Transition State ◽  
Mbh Reaction

An new overall lower energy pathway for the amine-catalysed Morita-Baylis-Hillman reaction is proposed from computations at the M06-2X/6-311++G(d,p) level. The pathway involves proton-transfer from the ammonium ion to the alkoxide formed from the aldol reaction through a seven-membered ring transition state (TS) structure followed by highly exothermic Hofmann<i> </i>elimination through a five-membered ring TS structure to form the product and also release the catalyst to carry on with the process all over again.

Mukaiyama Aldol Reaction Catalyzed by (Benz)imidazolium-Based Halogen Bond Donors

2020 ◽  
Author(s):  
Revannath L. Sutar ◽  
Nikita Erochok ◽  
Stefan Huber
Keyword(s):  
Halogen Bond ◽  
Aldol Reaction ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol ◽  
Background Reaction ◽  
Strong Performance ◽  
The Stability ◽  
Elemental Iodine

A series of cationic monodentate and bidentate iodo(benz)­imidazolium-based halogen bond (XB) donors were employed as catalysts in a Mukaiyama aldol reaction. While 5 mol% of a monodentate variant showed noticeable activity, a <i>syn</i>-preorganized bidentate XB donor provided a strong performance even with 0.5 mol% loading. In contrast to the very active BAr<sup>F</sup><sub>4</sub> salts, PF<sub>6</sub> or OTf salts were either inactive or showed background reaction. Repetition experiments clearly ruled out a potential hidden catalysis by elemental iodine and demonstrated the stability of our catalyst over three consecutive cycles.

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