Pseudoindoxyl Alkaloids. -A wide variety of indoles is converted into synthetically useful 2,2-disubstituted indolin-3-ones through visible light induced photocatalyzed aerobic oxidation/semipinacol rearrangement. Furthermore, a chiral version of the reaction is presented giving moderate enantioselectivities. -(DING, W.; ZHOU, Q.-Q.; XUAN, J.; LI, T.-R.; LU*, L.-Q.; XIAO, W.-J.; Tetrahedron Lett. 55 (2014) 33, 4648-4652, http://dx.
Copper(II) triflate/(R,R)‐Pybox has been used as catalytic system in the synthesis of 1‐tosyl‐2‐acyl‐3‐ethynylindolins in high yields and excellent dia‐ and enantioselectivities form corresponding acylsulfur ylides and 4‐ethynyl‐1‐tosyl‐1,4‐dihydro‐2H‐benzo[d][1,3]oxazin‐2‐ones.
An asymmetric conjugate addition of 2‐oxoindole‐3‐carboxylates to 2‐activated phthalimidoacrylates using a bifunctional cinchona‐derived thiourea as the catalyst is presented.
This is the first example of [3 + 2] cycloaddition/ ring contraction sequence under transition‐metal‐free conditions yielding the title spiro compounds.
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