59540-38-4

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 287481-44-1 methyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-2-bromoacetate 
• 67-56-1 methanol 

Downstream Products

• 50710-14-0 methyl 5-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxylate 
• 100246-19-3 (Z)-2-bromo-3-(4-nitrophenyl)prop-2-en-1-ol 
• 1380159-32-9 N-(5-bromo-2-methylphenyl)-N-[(Z)-2-bromo-3-(4-nitrophenyl)prop-2-enyl]-4-methylbenzenesulfonamide 
• 7515-15-3 methyl 3-(4-nitrophenyl)-2-propynoate 

Relevant academic research and scientific papers

α-hypervalent iodine functionalized phosphonium and arsonium ylides and their tandem reaction as umpolung reagents

α-Hypervalent iodine functionalized phosphonium and arsonium ylides 2 can be used as umpolung ylides to react with nucleophiles to give α-heteroatom substituted ylides 4 in good yields. The nucleophilic substitution - Wittig tandem reaction of 2 can occur smoothly to provide an efficient method for the synthesis of (Z)-α-halo-α,β-unsaturated enoates or enones 6, stereoselectively.

A highly stereoselective synthesis of (E)-α-bromoacrylates

Novel reagent, methyl bis(2,2,2-trifluoroethoxy)bromophosphonoacetate (5a), was designed and prepared in order to efficiently synthesize (E)-α-bromoacrylates 7, from which widely useful precursors for various C-C bond formations were prepared. Horner-Wadsworth-Emmons (HWE) reaction of various aldehydes with 5a in the presence of t-BuOK and 18-C-6 gave corresponding (E)-α-bromoacrylate derivatives with high stereoselectivity and excellent yield. Using the product (E)-α-bromoacrylate 7s as a key intermediate, we succeeded in developing the most effective route of plaunotol synthesis via Suzuki cross-coupling. (C) 2000 Elsevier Science Ltd.