Enolate Formation from α-Iodoaldehydes and α-Iodoketones by Means of Allylsilane−Titanium Tetrachloride and Its Application to an Aldol Reaction

1998 ◽  
Vol 63 (13) ◽  
pp. 4558-4560 ◽  
Author(s):  
Katsuya Maeda ◽  
Hiroshi Shinokubo ◽  
Koichiro Oshima
Keyword(s):  
Titanium Tetrachloride ◽  
Aldol Reaction

scholarly journals Halogeno Aldol Reaction of Ethyl Vinyl Ketone and Aldehydes Mediated by Titanium Tetrachloride

Molecules ◽  
2000 ◽  
Vol 5 (12) ◽  
pp. 1408-1416 ◽  
Author(s):  
Han-Xun Wei ◽  
Subramanian Karur ◽  
Guigen Li
Keyword(s):  
Titanium Tetrachloride ◽  
Aldol Reaction ◽  
Vinyl Ketone ◽  
Ethyl Vinyl

C19 quassinoid model studies: Preparation of trans-perhydroindans via a vinylogous Mukaiyama aldol – free-radical cyclization route

2004 ◽  
Vol 82 (2) ◽  
pp. 314-317 ◽  
Author(s):  
Matthew G Donahue ◽  
David J Hart
Keyword(s):  
Free Radical ◽  
Acid Treatment ◽  
Titanium Tetrachloride ◽  
Aldol Reaction ◽  
Radical Cyclization ◽  
Asymmetric Induction ◽  
Model Studies ◽  
Mukaiyama Aldol ◽  
Relationship Of ◽  
The Relationship

Aldehyde 9 was prepared in 5 steps from 3,5-dimethylbenzoic acid. Treatment of 9 with ketene acetals 10 and 19 and titanium tetrachloride gave free-radical cyclization substrates 11 and 20 in 67% and 51% yields, respectively. Tri-n-butylstannane-mediated cyclization of 11 and 20 gave trans-perhydroindans 14 and 21 in 60% and 63% yields, respectively. The relationship of these studies to an approach to C19 quassinoids is discussed.Key words: vinylogous Mukaiyama aldol reaction, free-radical cyclization, trans-perhydroindans, C19 quassinoids, 1,2-asymmetric induction.

Ammonolysis of titanium tetrachloride in liquid ammonia

1976 ◽  
Vol 73 ◽  
pp. 849-851 ◽  
Author(s):  
Thomas Kottarathil ◽  
Gérard Lepoutre
Keyword(s):  
Liquid Ammonia ◽  
Titanium Tetrachloride

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.

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