1,7-Asymmetric induction of chirality in a Mukaiyama aldol reaction using π-allyltricarbonyliron lactone complexes: highly diastereoselective synthesis of α-substituted β-hydroxy carbonyl compounds

2000 ◽  
pp. 1677-1683 ◽  
Author(s):  
Steven V. Ley ◽  
Edward A. Wright
Keyword(s):  
Carbonyl Compounds ◽  
Aldol Reaction ◽  
Asymmetric Induction ◽  
Diastereoselective Synthesis ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol

Diastereoselective Synthesis of Cephalotaxus Esters via Asymmetric Mukaiyama Aldol Reaction

2017 ◽  
Vol 19 (9) ◽  
pp. 2250-2253 ◽  
Author(s):  
Guo-Zhen Ma ◽  
Peng-Fei Li ◽  
Lu Liu ◽  
Wei-Dong Z. Li ◽  
Li Chen
Keyword(s):  
Aldol Reaction ◽  
Diastereoselective Synthesis ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol

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.

scholarly journals Design and Synthesis of a Chiral Halogen-Bond Donor with a Sp3-Hybridized Carbon–Iodine Moiety in a Chiral Fluorobissulfonyl Scaffold

Molecules ◽  
2020 ◽  
Vol 25 (19) ◽  
pp. 4539
Author(s):  
Hiroto Uno ◽  
Kohei Matsuzaki ◽  
Motoo Shiro ◽  
Norio Shibata
Keyword(s):  
Halogen Bond ◽  
Aldol Reaction ◽  
Asymmetric Induction ◽  
Nmr Titration ◽  
Titration Experiment ◽  
Mukaiyama Aldol Reaction ◽  
Design And Synthesis ◽  
Mukaiyama Aldol

The first example of a chiral halogen-bond donor with a sp3-hybridized carbon–iodine moiety in a fluorobissulfonyl scaffold is described. The binaphthyl backbone was designed as a chiral source and the chiral halogen-bond donor (R)-1 was synthesized from (R)-1,1′-binaphthol in 11 steps. An NMR titration experiment demonstrated that (R)-1 worked as a halogen-bond donor. The Mukaiyama aldol reaction and quinoline reduction were examined using (R)-1 as a catalyst to evaluate the asymmetric induction.

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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