66806-69-7Relevant articles and documents
Tuning the Reactivity of Functionalized Diallylic Alcohols: Br?nsted versus Lewis Acid Catalysis
Lempenauer, Luisa,Du?ach, Elisabet,Lemière, Gilles
supporting information, p. 10285 - 10288 (2017/08/07)
The chemodivergent reactivity of bifunctional, enol thioether-containing diallylic alcohols in acidic medium is disclosed, highlighting the difference between strong Lewis acid and mild Br?nsted acid catalysis. In the presence of bismuth(III) triflate, allylic alcohol activation affords diversely substituted cyclopentenones in a Nazarov-type electrocyclization, whereas activation of the thioenol ether by p-toluenesulfonic acid provides an entry to α-sulfenylated β,γ-unsaturated ketones. Both methods represent a facile access to the corresponding products under mild conditions, using inexpensive and non-toxic catalytic systems.
Remarkably chemoselective reduction of unmodified Baylis-Hillman adducts by InCl3/NaBH4: Application to the stereoselective synthesis of trisubstituted alkenones including two alarm pheromones
Das, Biswanath,Banerjee, Joydeep,Chowdhury, Nikhil,Majhi, Anjoy,Holla, Harish
, p. 1879 - 1882 (2008/02/08)
A novel, convenient and solely stereoselective synthesis of trisubstituted E-alkenones has been achieved by InCl3/NaBH4 mediated chemoselective reduction of unmodified Baylis-Hillman adducts derived from vinyl ketones and cycloalkenones for the first time. The efficiency of this methodology in the practical synthesis of (S)-(+)-manicone and (S)-(+)-normanicone, two alarm pheromones of Manica ants, has been demonstrated. Georg Thieme Verlag Stuttgart.
Stereochemistry of Addition of Allylic Grignard Reagents to α,β-Ethylenic Ketones
Zair, Touriya,Santelli-Rouvier, Christiane,Santelli, Maurice
, p. 2686 - 2693 (2007/10/02)
The stereochemistry of the addition of allylic Grignard reagents, (mainly crotylmagnesium chloride) to various conjugated enones has been investigated and a compact transition state is postulated.For s-cis-enones bearing no bulky substituents, a boat transition state, involving a trans-crotylmagnesium chloride, occurs leading to erythro-1,5-hexadien-3-ols as the major or only product.