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Chem. , 1980, 102, 3298. M. Kobayashi and E. Negishi, J. Org. , 1980, 45, 5223. General and Synthetic Methods 44 illustrated by a synthesis of the natural product 'mokupalide' [(60);>95% regioand stereo-chemically pure]. 0 Reagents: i, Mg-THF; ii, ZnBr,; iii, 0 -3 mol% Cl,Pd(PPh,), :Bu',AlH (1: 2) Br The research groups of Trost and Stille have demonstrated in related studies that allylic stannanes undergo palladium-catalysed cross-coupling with allylic acetatesZo0or allylic bromidesZo1to furnish 1,5-dienes in variable yields.
1980, 45, 4260. HF Scheme 59 reactant, branching at the carbon p- to phosphorus in the ylide, or at the a'-position of the carbonyl partner, tend to diminish stereoselectivity. Substituted cyclohex-2-enols of the type (48) can be prepared from a,& epoxycyclohexanones. g. g. Scheme 61). g. lS4The method is particularly useful for the preparation of allylic alcohols with terminal double bonds. The reaction of hypochlorous acid in dichloromethane with olefins that are at least trisubstituted gives predominantly allylic chlorides rather than + LOH LSnBu ' i,ii Ph Ph Ph OH Reagents: i, NaH-CS,-MeI; ii, Bu",SnH; iii, m-CPBA; iv, H' Scheme 62 15* 153 154 J.
Chem. Soc. , 1980, 53, 1625. T. Hirao, T. Masunaga, Y. Ohshiro, and T. , 1980,21, 3595. G . Axelrad, S. Laosooksathit, and R. Engel, Synth. , 1980, 10, 933. A. Gupta, K. Sacks, S. Khan, B. E. Tropp, and R. Engel, Synrh. , 1980,10, 299. -J. Tilhard, H. Ahlers, and T. , 1980, 21, 2803. Saturated and Unsaturated Hydrocarbons a XCHZPOPh;! g. g. 12' Both processes are compatible with cyano and ester groups, and when terminal silicates are used stereoselectivity is very high (>99%). Primary alcohols give the highest yields of enol ethers, whereas tertiary alcohols do not react, and allylic alcohols give the particularly useful ally1 vinyl ethers.