A concise synthesis of tubuphenylalanine and epi-tubuphenylalanine via a diastereoselective Mukaiyama aldol reaction of silyl ketene acetal

2016 ◽  
Vol 14 (3) ◽  
pp. 913-919 ◽  
Author(s):  
Yunjeong Park ◽  
Mikyung Sim ◽  
Tong-Shin Chang ◽  
Jae-Sang Ryu
Keyword(s):  
Aldol Reaction ◽  
Synthetic Route ◽  
Mukaiyama Aldol Reaction ◽  
Ketene Acetal ◽  
Mukaiyama Aldol

A concise auxiliary-free synthetic route towards tBu-tubuphenylalanine (tBu-Tup) and tBu-epi-tubuphenylalanine (tBu-epi-Tup) has been developed via a diastereoselective Mukaiyama aldol reaction of silyl ketene acetal.

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.

ChemInform Abstract: Mukaiyama Aldol Reaction of Trimethylsilyl Enolate with Aldehyde Catalyzed by CuI.

ChemInform ◽  
2013 ◽  
Vol 44 (22) ◽  
pp. no-no
Author(s):  
Hima Rani Kalita ◽  
Arun Jyoti Borah ◽  
Prodeep Phukan
Keyword(s):  
Aldol Reaction ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol

ChemInform Abstract: Study of the Lanthanide-Catalyzed, Aqueous, Asymmetric Mukaiyama Aldol Reaction.

ChemInform ◽  
2012 ◽  
Vol 43 (43) ◽  
pp. no-no
Author(s):  
Yujiang Mei ◽  
Derek J. Averill ◽  
Matthew J. Allen
Keyword(s):  
Aldol Reaction ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol

The Chelation-controlled Mukaiyama Aldol Reaction of Chiral α- and β-Alkoxy Aldehydes

2014 ◽  
Vol 43 (1) ◽  
pp. 2-10 ◽  
Author(s):  
Gheorghe-Doru Roiban ◽  
Adriana Ilie ◽  
Manfred T. Reetz
Keyword(s):  
Aldol Reaction ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol
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