Naphthylmagnesium bromide

Solladie and coworkers avoided the use of a sulfinyl chloride when they prepared (— )-menthyl 1-naphthalenesulfinate in an overall yield of 45% by the reaction of thionyl diimidazole, obtained from imidazole and thionyl chloride, with 0.7 equivalent of ( — )-menthol followed by 1 equivalent of 1-naphthylmagnesium bromide (equation 4). 

Treatment of a thirteen-membered lactam with 1-naphthylmagnesium bromide forms both a cyclic enamine and the amino ketone412. Imides of dicarboxylic acids produce with organometallic reagents cyclic enamino compounds such as 108 (n = 1, 2)413-418. 

The nickel-catalyzed cross-coupling of 2-methyl-1-naphthylmagnesium bromide 32a has been extended to the asymmetric synthesis of ternaphthalenes (Scheme 2-21) [41]. The reaction with 1,5- and 1,4-dibromonaphthalenes in the presence of the same catalyst, nickel/(S)-(R)-9, produces the corresponding optically active ternaphthalenes with 99% ee (35) and 95% ee (36), respectively, together with a small amount of meso compounds. 

Asymmetric conjugate addition of RiCuLij The chiral crotonyl ester 1, prepared from (+ )-camphor by addition of 1-naphthylmagnesium bromide followed by esterification with crotonic acid, undergoes conjugate addition with BuaCuLi at -25° to give the adduct 2 in 95% de. Reduction of 2 with LiAUtj gives (S)-3-... 

Grignard reaction. The reagent reacts with benzylmagnesium chloride, phenyl-magnesium chloride, phenyllithium, and 1-naphthylmagnesium bromide to give... 

The ligand coupling reaction of homochiral sulfoxides [(116) - (119)] with 1-naphthylmagnesium bromide led to the atropoisomeric l,r-binaphthyl derivatives [(120) - (123)] in good yields (65-90%) and with good to high enantiomeric excess (60-95%)78... 

Somewhat between diastereoselective and enantioselective approaches is the Cram s synthesis involving the oxazolines with chiral alkoxide leaving groups [26]. In this manner, bromine in oxazoline 596 was substituted with sodium alkoxides, derived from readily available natural alcohols such as menthol (597), fenchyl alcohol (598), bomeol (599), quinine (600), and quinidine (601) to give the respective chiral oxazolines 602-606, Scheme 10. The Meyers reaction of oxazolines 602-606 and 1-naphthylmagnesium bromide (608) was effected at low temperatures (-42 °C) affording the expected biaryl 609 with respective chiral induction. 

S,3S)-l,4-Bis(l-naphthyl)-2,3-butanediol(3c) To the 1-naphthylmagnesium bromide solution, which was prepared from 2.72 g (112 mmol) of Mg, 20.45 g(98.8 mmol) of 1-bromonaphthalene and 60 ml of THF, was added 9.40 g of (2), 60 ml of benzene and 0,2 mmol of Li2CuCl in 2 ml of THF and refluxed for 7 h. The mixture was filtered after the addition of saturated aqueous NH Cl solution. The residue was extracted with ether in a Soxhlet extractor. The combined filtrate and extract were dried over Drierite, evaporated and hydrolyzed with cone. 

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