stereo_peri
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- かずき こやぎ
- 9 years ago
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1 I. (ISB ) () (i) iels-alder,3- ( ) [4] diene dienopile iels-alder (e.. nisesky ) (e.. ) 00, 80% 50, % 0, 8 9% 3 Si nisesky's diene (e.. ) J. Am. em. Soc. 00, 4, Acid (0%) 8, 4 85% yield 94% ee Ar Ar Ar B T Acid Lewis Brønsted α,β- iels-alder iels-alder endo- exo- endo-! exo- 50, % 50, 0 dys 85% 5, 4 80% 50, 0.5 % diene dienopile endo- exo- TS exo TS endo
2 (ii) iels-alder iels-alder 0, 4 90% tlyst 88% yield 9% ee tlyst Br Ti Br (iii),3-,3- Y X Y X or X Y X Y X, Y,,,, S 4,3- [3] t t 0, 98% 5, 5 d % t t Lewis () Woodwrd-omnn (i) - π-!!! 4!! 5! 4!!! 5! 4! ntiondin ondin π- π- (M) (LUM) (ii) (M-LUM) M LUM M, LUM
![[3] t t 0, 98% 5, 5 d % t t Lewis () Woodwrd-omnn (i) - π-!!! 4!](/docs-images/47/20501357/images/page_2.jpg "! 5! 4!!! 5! 4! ntiondin ondin π- π- (M) (LUM) (ii) (M-LUM) M LUM M, LUM")
3 . [4] M ()LUM () 3 4 M () LUM () 5 (,4,5,) π- π- endo LUM ()M () 3 4 LUM() M () 5 M ()LUM () ( )! * 3 ) ( ) ) M( * )M() LUM( * )LUM() LUM M! * exciplex product 3 [4] LUM ( * ) LUM () M ( * ) M () o ection o ection π-. []! LUM ( * ) LUM () M ( * ) M () LUM( * )LUM(), M( * )M() M()LUM() (iii) Woodwrd-omnn ) (π or σ) ( ) ) π- π- σ- 3) ( or )
![* exciplex product 3 [4] 3 4 5 LUM ( * ) LUM () 3 4 5 M ( * ) M () o ection o ection π-.](/docs-images/47/20501357/images/page_3.jpg "[]! LUM ( * ) LUM () M ( * ) M () LUM( * )LUM(), M( * )M() M()LUM() (iii) Woodwrd-omnn")
4 π- suprcil ntrcil σ- sp 3 sp 3 suprcil ntrcil. iels-alder d c e!4s c d e!s c e d Woodwrd-omnn ) (4q)s (4r) ) (4q)s (4r) q, r iels-alder [π4s πs] (4q)s (4r) 0 iels-alder [πs σs σs] (4q)s 3 (4r) 0 3 [] [πs πs] (4q)s (4r) 0. iels-alder e c d "s!s!s 3. [] c d c d [π4s πs] [πs σs σs] c d c d c c d d!s!s [πs πs] 4
![(4r) 0 iels-alder [πs σs σs] (4q)s 3 (4r) 0 3 [] [πs πs] (4q)s (4r) 0.](/docs-images/47/20501357/images/page_4.jpg "iels-alder e c d \"s!s!s 3. [] c d c d [π4s πs] [πs σs σs] c d c d c c d d!s!s [πs πs] 4")
5 (c) (i) 0, 30 0, 8 '! ( ) '! " (ii) (conrottory) vs (diottory) ' diottory 9, ( ) 80 (iii) l l l l l 4$%& conrottory π- M π- LUM σ- M (# )*#,-.[!4] '"# /-.[!s "],-.[!s] $%&!"# /-.[!4s "s] 8$%&,-.[!8] '"# /-.[!s "]!"# '"#!"#,-.[!4s] /-.[!s "s],-.[!] /-.[!4s "],-.[!8s] /-.[!s "s] 3 Si l (S ) Fel 3 3 Si Fel 3 3 Si zrov Fel 3 or 5
![conrottory π- M π- LUM σ- M (# )*#,-.[!4] '"# /-.[!s "],-.[!s] $%&!"# /-.[!4s "s] 8$%&,-.](/docs-images/47/20501357/images/page_5.jpg "[!8] '\"# /-.[!s \"]!\"# '\"#!\"#,-.[!4s] /-.[!s \"s],-.[!] /-.[!4s \"],-.[!8s] /-.[!s \"s] 3 Si l (S ) Fel 3 3 Si Fel 3 3 Si zrov Fel 3 or 5")
6 (d) (i) [,n]- [,5]-ydroen sit [,]-ydroen sit (ii) (suprcil) vs (ntrcil) (iii) [,n] Ac [,3] Ac inveron [,5] [,5] suprcil pt pt ntrcil Woodwrd-omnn Woodwrd-omnn. σ. σ [σs] [! 4 s ] [! ] 3. [ [ " s ] " s ] [πs] [π] 4. Woodwrd-omnn [,n] n 3 n 5 [ ( )] n S not detected S evidence o suprcil ptwy evidence o ntrcil ptwy [,3]- [! s ] A [ " s ] [! s ] B [ " ] [! ] [ " s ] A B s [σ] p [σ] [,n]- Woodwrd-omnn!"# 4!"#!"# 8!"# [,3] [,] [,4] [,4] [,5] [,] [,] [,] etc. i r i r $% [ s " 0 s ] [ " 0 ] [ # s ] or [ " s ] [ s # ] or [ s " ] [ s # 4 s ] [ # 4 ] [ # s ] [ s # ] r i r i &'(% [ " 0 s ] [ s " 0 ] [ s # s ] or [ s " s ] [ # ] or [ " ] [ # 4 s ] [ s # 4 ] [ s # s ] [ # ] s:, :, r:, i:
![s ] A [ " s ] [! s ] B [ " ] [! ] [ " s ] A B s [σ] p [σ] [,n]- Woodwrd-omnn!"# 4!"#!"# 8!"# [,3] [,] [,4] [,4] [,5] [,] [,] [,] etc.](/docs-images/47/20501357/images/page_6.jpg "i r i r $% [ s \" 0 s ] [ \" 0 ] [ # s ] or [ \" s ] [ s # ] or [ s \" ] [ s # 4 s ] [ # 4 ] [ # s ] [ s # ] r i r i &'(% [ \" 0 s ] [ s \" 0 ] [ s # s ] or [ s \" s ] [ # ] or")
7 (iv) [m,n]- ' m n [m,n] '.. m n [m,n]- ope [3,3]- m n xy-ope Bse [3,3] drivin orce 8-crown- 0 K K K lisen [ s ] [ s ] [ " s ] > [ " s ] [ " s ] [ " s ] cir-orm ot-orm or [3,3] [3,3] % [3,5] Irelnd-lisen 40 Bse 4 0 9% Li(i-Pr) nti 0 min 9%
![8-crown- 0 K K K lisen [ s ] [ s ] [ " s ] > [ " s ] [ " s ]](/docs-images/47/20501357/images/page_7.jpg "[ \" s ] cir-orm ot-orm or [3,3] [3,3] 80 8 9% [3,5]")
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PowerPoint プレゼンテーション
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