A Convenient Protocol for the α-Iodination of α,β-Unsaturated Carbonyl Compounds with I₂ in an Aqueous Medium

Abstract

P r o t o c o l f o r t h e a -I o d i n a t i o n o f a , b -U n s a t u r a t e d C a r b o n y l C o m p o u n d s w i t h I

Construction of the Tricyclic A-B-C Core of the Veratrum Alkaloids

“…5 As we have reported, 6 using the Schaus 7 protocol, allyl borane 11 in the presence of catalytic R -Br 2 BINOL , to deliver the alcohol 12 in high yield and 95% ee. For this conversion to be practical, the catalyst ($200/gram) needed to be recycled.…”

“…Following the reported procedure, 5 2-cyclohexenone (35.0 g, 0.365 mol) was dissolved in a 1:1 mixture of THF:H 2 O and stirred at 0 °C for 5 min. Next, K 2 CO 3 (60.375 g, 0.438 mol) was added, followed by DMAP (8.893 g, 7.29 mmol).…”

Pd(PPh3)4/AgOAc-catalyzed one-pot synthesis of substituted 3,4-dihydronaphthalen-1(2H)-ones

“…Reagents and solvents investigated for the reaction were I 2 / 4-dimethylaminopyridine (DMAP)/K 2 CO 3 /tetrahydrofuran (THF)-H 2 O [16] and I 2 /pyridine/CCl 4 [17]. The results showed that the reaction was mild at ambient temperature while using I 2 /DMAP/K 2 CO 3 /THF-H 2 O or I 2 /pyridine/ CCl 4 .…”

“…2-Iodocyclohex-2-enone (2a) was prepared using Krafft and Cran's method [16]; 2-iodo-4,4-dimethylcyclohex-2-enone (2b) was prepared using Felpin's method [17]. General procedure for the one-pot synthesis of 3,4-dihydronaphthalen-1(2H)-ones 3-9…”

Vinylic Halogenation in 4‐Alkylidenazetidin‐2‐ones

“…[9] Direct bromination of more complex substrates such as uracils [10] or β-amino-and β-alkoxy α,β-unsaturated compounds, has been accomplished more frequently, [11] as in the cases of the bromination of 2-alkylidenetetrahydrofurans and 2-alkylidenepyrrolidines, [12] β-butoxyvinyl trifluoromethyl ketone [13] and β-aminovinyl chlorodifluoromethyl ketones. [14] To the best of our knowledge, vinylic substitution on β-amido α,β-unsaturated esters has never been reported in the literature.…”