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Download Organic Synthesis–2. Plenary Lectures Presented at the by S. Sarel PDF

By S. Sarel

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1 h o u r , a n dt h e n a l k y l a t e d w i t h e t h y l i o d i d e , t h e k e t o n e was f o r m e d i n 7 6 % e e ( 2 5 ) ( F i g . 2 1 ) . Α. I. MEYERS 1266 R-CH2 H,^ R"X LDA S-ketone E-isomer R"X -> Fig. R-ketone 20 Several additional examples behaved s i m i l a r l y in that a f t e r heating the metalloenamines, a l k y l a t i o n s gave α - s u b s t i t u t e d ketones i n 80-90% e e . T h i s appears t o i n d i c a t e t h a t t h e l i t h i o enamines a r e formed k i n e t i c a l l y i n an u n f a v o r a b l e r a t i o and by heating i t i s p o s s i b l e t o overcome t h e r o t a t i o n a l b a r r i e r f o r m i n g a more f a v o r a b l e thermodynamic r a t i o .

W. S c o t t , S y n t h e s T ? , 329 ( 1 9 7 8 , . H . Kagan and J . C . F i a u d , "Asymmetric S y n t h e s e s " , T o p i c s i n S t e r e o c h e m i s t r y . V o l . 1 0 , E. E l i e l and N . L . A l l i n g e r , e d . , W i l e y - I n t e r s c i e n c e , 1 9 7 8 . 1268 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. 22. 23. 24. 25. 26. Α. I. MEYERS Α . I. M e y e r s , R . L . N o l e n , D . L . T e m p l e , a n d E . D . M i h e l i c h , J . O r g . C h e m .

M e y e r s and C . E . W h i t t e n , H e t e r o c y c l e s , 4 , 1 6 8 7 ( 1 9 7 6 ) . A . I. M e y e r s a n d C . E . W h i t t e n , T e t r a h e d r o n L e t t e r s , 1 9 4 7 ( 1 9 7 6 ) . S . Yamada, e t a l . , J . Am. Chem. S o c , 9 8 , 7450 ( 1 9 7 6 ) . J . B. J o n e s and A . J . I r w i n , J . Am. Chem. S o c , 9 9 , 556, 1625 ( 1 9 7 7 ) . A . I. M e y e r s a n d J . S l a d e , S y n t h e t i c C o m m . , 601 and u n p u b l i s h e d w o r k . A . Horeau, et a l . , B u l l .

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