Download e-book for iPad: General and synthetic methods Volume 8 by G Pattenden

By G Pattenden

ISBN-10: 1847556205

ISBN-13: 9781847556202

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Extra info for General and synthetic methods Volume 8

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Scheme 49) Reagents: i, BuLi; ii, Me,CHCH,CHO; iii, TsOH; iv, NaIO,; v, PhMe, reflux Scheme 49 On lithiation, the a-silyl-ketimine (75) reacts with aldehydes and ketones as a regiospecific ethyl methyl ketone aldol equivalent. g. Scheme 50). 83:17 (75) Reagents: i, LDA; ii, w o ; iii, H30+,silica gel Scheme 50 119 T. Mukaiyama, M. Ohshima, and T. Nakatsuka, Chem. , 1983,1207. Y. Ueno, L. D. S. Yadav, and M. Okawara, Chem. , 1983, 831. 121 J. Durman, J. Elliott, A. B. McElroy, and S. , 1983,24,3927 lzz A.

J. Burton and D. G. Cox, J . Am. Chem. , 1983,105,650. S . Martin, R. -F. , 1983,24, 5615. 83 A. S. Kende and P. Fludzinski, J. Org. , 1983,48, 1384. & T. Ishihara, M. Yamana, and T. , 1983,24, 5657. I11... 0 It CF2ClCPh L FJ+,/op(oR)2 II R=Ph Ph (40) 0 Ph (39)R =Ph ( 4 1 ) R =Et Ph (42) Reagents: i, HP(Q)(QR),, Et,N; ii, Bun,CuLi, TMEDA; iii, CH,=CHCH,Br difluoromethyl ketones (43) can be converted into the corresponding 2,2difluoro-enol silyl ethers (44) by treatment with zinc and trimethylsilyl chloride in acetonitrile at 60°C.

Llu G. A . Flynn, J . Org. , 1983,48, 4125. lo7 J. General and Synthetic Methods 28 OH i L -iii O (62) Reagents: i, Ph,P= CH,; ii, H30+;iii, KOBu' Ley and Simpkins have reported an approach to synthetically important vinyl sulphones using Peterson olefination. ll1 Following lithiation, phenylsulphonyl(trimethylsily1)methane reacts smoothly with aldehydes and ketones at -78°C to afford (E/Z)-isomeric mixtures of vinyl sulphones such as (63) directly. Other functional groups such as esters, acetals, epoxides, and silyl ethers are inert under the reaction conditions.

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General and synthetic methods Volume 8 by G Pattenden

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