Asymmetric syntheisis

8/20/2019 Asymmetric syntheisis

http://slidepdf.com/reader/full/asymmetric-syntheisis 1/155

Asymmetric Synthesis



Selective Formation of Alkenes: Julia Olefination









Selective Formation of Alkenes: Stereospecific Eliminations



Stereospecific Eliminations: Peterson Elimination



Stereospecific Eliminations: Peterson Elimination



Selective Formation of Alkenes: Wittig Reaction












Z -Selective Wittig Reaction



Z -Selective Wittig Reaction



E -Selective Wittig Reaction



E -Selective Wittig Reaction



Selective Formation of Alkenes: Summary



Stereoselectivity in Cyclic Molecules



Cyclic Molecules: Stereocontrol in Six-mebered Rings



Stereocontrol in Six-mebered Rings: Cyclohexanone












Stereocontrol in Six-mebered Rings: Cyclohexenes


















Reactions on Small Rings: Four-membered Rings



Reactions on Small Rings: Five-membered Rings









Reactions on Small Rings: Cyclohexene Epoxides





















Stereoselectivity in Bicyclic Compounds: Bridged Rings









Stereoselectivity in Bicyclic Compounds: Fused Rings



Stereoselectivity in Bicyclic Compounds: trans-Fused Rings



Stereoselectivity in Bicyclic Compounds: cis-Fused Rings















Stereoselectivity in Bicyclic Compounds: cis-Decalins









Stereoselectivity in Bicyclic Compounds: Spirocycles`



Reaction with Cylic Intermediate or Cyclic Transition States`



Reaction with Cylic Intermediate or Cyclic Transition States















Diastereoselectivity in Rings: Summary



Diastereoselectivity



Diastereoselectivity: Stereospecific Reactions



Diastereoselectivity: Reactions of Alkanes












Diastereoselectivity: Stereoselective Reactions



Diastereoselectivity: Stereoselective Reactions



Draw a Single Diastereomer



Prochirality: Prochiral Center



Prochirality: Stereotopic Face



Prochirality: Stereotopic Face



Prochiral Faces and Groups: R/S -type System



Diastereoselectivity: Addition to Carbonyl Groups



Addition to Carbonyl Groups: Conformation of Chiral Aldehydes



Major Product Comes from Most Reactive Conformer



Addition to Carbonyl Groups: Felkin-Anh Model



Addition to Carbonyl Groups: Effect of Electronegative Atoms



Addition to Carbonyl Groups: Effect of Electronegative Atoms



Addition to Carbonyl Groups: Using Felkin-Anh Model



Addition to Carbonyl Groups: Chelation















Stereoselective Reactions of Acyclic Alkenes



Stereoselective Reactions of Acyclic Alkenes: the Houk Model



Stereoselective Reactions of Acyclic Alkenes: Epoxidation









Stereoselective Reactions of Acyclic Alkenes: Enolate Alkylation



Stereoselective Reactions of Acyclic Alkenes: Aldol Reactions







Zimmerman-Traxler chair-like transition state






Stereoselective Reactions of Acyclic Alkenes: Enolization

S l i R i f A li Al E li i



Stereoselective Reactions of Acyclic Alkenes: Enolization

Si l E i f Di l i R i



Single Enantiomers from Diastereoselective Reactions

Si l E ti f Di t l ti R ti



Single Enantiomers from Diastereoselective Reactions

St t d S th i f P idi S th i



Structure and Synthesis of Penaresidin: Synthesis

St t d S th i f P idi S th i



Structure and Synthesis of Penaresidin: Synthesis

St t d S th i f P idi St fi ti



Structure and Synthesis of Penaresidin: Stereo-confirmation

Structure and Synthesis of Penaresidin Stereo confirmation



Structure and Synthesis of Penaresidin: Stereo-confirmation

Asymmetric Synthesis: Nature is Asymmetric



Asymmetric Synthesis: Nature is Asymmetric

Asymmetric Synthesis: Drug are Asymmetric



Asymmetric Synthesis: Drug are Asymmetric

Asymmetric Synthesis: the Chiral Pool
















Asymmetric Synthesis: Resolution



Asymmetric Synthesis: Resolution

Asymmetric Synthesis: Chiral Auxiliaries

















sy et c Sy t es s C a u a es

Asymmetric Synthesis: Enantiomeric Excess



y y

!"# %&'(&)*

Asymmetric Synthesis: Alkylation of Enolates



y y y






y y




y y

Asymmetric Synthesis: Chiral Reagents



y y g

Asymmetric Catalysis: Reduction of Ketones















Asymmetric Catalysis: Reduction of Alkenes























Asymmetric Catalysis: Sharpless Epoxidation

















Asymmetric Catalysis: Sharpless Dihydroxylation














Asymmetric Catalysis: Carbon–Carbon Bond Formations



Asymmetric C–C Bond Formations: Conjugate Addition



Asymmetric C–C Bond Formations: Organocatalysis



Asymmetric C–C Bond Formations: Organocatalysis





Asymmetric Aldol Reactions: Chiral Auxiliary



Asymmetric Aldol Reactions: Proline Catalyst





Enzymes as Catalysts



Asymmetric Synthesis: Summary



Documents

Asymmetric syntheisis