1934 General Motors GM Fisher Body Service Manual by General Motors

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OC results in Methods f o r t h e h i g h l y r e g i o - a n d s t e r e o - s e l e c t i v e formation of e n o l a t e s and t h e i r d e r i v a t i v e s are i m p o r t a n t t a r g e t s i n o r g a n i c s y n t h e s i s which c o n t i n u e t o a t t r a c t a t t e n t i o n . A w i d e l y u s e d two- s t e p procedure f o r t h e s e l e c t i v e formation of k i n e t i c a l l y g e n e r a t e d s i l y l e n o l e t h e r s i n v o l v e s t h e s l o w a d d i t i o n o f c a r b o n y l compounds t o l i t h i u m d i - i s o p r o p y l a m i d e (LDA) a t -78 silylation.

E. e r y t h r o : threo = 90 :10 \OMe iii,CHZNZ Reagents: i , BunLi or L D A ; i i , 3 N H2S04 Scheme 47 MeS w S0;Tol SO~TOI .. '+R"P, OMe Reagents: i , Me3SiCH2MgCI,0°Cjii, NaH,HMPAj i i i , Bu"Li, HMPA,R2X; i v , [ o l Scheme 49 30 General and Synthetic Methods CN Reagents: i, P l - 1 5 4 , ~HMPA; ~ NMe2 (70) ii, m-CIC6H4C03H; iii, A , CaC03 Scheme 50 R Reagents: i, TosCHzNC; ii, K O d , $X ; iii, H30' Scheme 51 Reagents i, CO, [Pd ( PPh3I2 CIzl. Zn / C u ,[ Cp2TiC12J Scheme 52 1: Saturated and Unsaturated Hydrocarbons 31 substituted enones, such as sponge constituent (74) (Scheme 53).

5 2 The u s e o f t h e more h i n d e r e d b a s e l i t h i u m t - o c t y l - t - b u t y l a m i d e (LOBA) i s e v e n more e f f e c t i v e , and i n a d d i t i o n g i v e s e x c e l l e n t c o n t r o l o f enolate stereochemistry. A r e v e r s a l of s e l e c t i v i t y (Scheme 2 9 ) i s o b s e r v e d i n t h e p r e s e n c e o f HMPA, h o w e v e r , a r e s u l t c l o s e l y p a r a l l e l e d by t h e work o f T u r n e r e t a l . 54 The s u b s t i t u t e d z i r c o n i u m c a r b e n e c o m p l e x e s ( 4 1 ) a n d ( 4 2 ) r e a c t w i t h c y c l i c i m i d a t e s t o a f f o r d good y i e l d s o f e n o l e t h e r s (Scheme 3 0 ) .

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