reaction_review

reaction_review - ALKENES Br H2 (D2) Lindlar's cat Pd / C /...

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Br In general, E 1 and E 2 (for other alkenes) mCPBA 1) Hg(OAc) 2 2) NaBH 4 1) BH 3 2) H 2 O 2 NaOH HBr HBr AIBN H 2 Pd / C X 2 H 2 O X 2 ROH X 2 OsO 4 H 2 O 1) O 3 2) (CH 3 ) 2 S or H 2 O 2 HCCl 3 , KO t Bu CH 2 I 2 , Zn or O OH OH OH Br Br Br Br Br OH Br OR Br OH OH O O OH H Cl Cl H 2 (D 2 ) Lindlar's cat Pd / C / quinoline syn addition gives trans where applicable Na/NH 3 O K + ALKENES (±) (±) (±) (±) (±) (±) (±) (±) (±) Cycloaddition chemistry: – Diels-Alder – rxn with Ph–N 3 – rxn with diazomethane H 3 O + (ROH) OH not racemic but enantioenriched 1) (Ipc) 2 BH (enantiopure) 2) H 2 O 2 , NaOH
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H 3 C OH H 3 C I H O 1) CH 3 MgBr 2) H 2 O 1) BH 3 2) H 2 O 2 /NaOH H 3 C OH TsCl, pyridine (deprotonate) H 3 C NaOH (S N 2) H 3 C H 3 C Cl H 3 C OTs O 2 (dry) or DMP (mildest) SOCl 2 , pyridine H O H 3 C H 3 C O O H 3 O + harsh H 3 C O CH 3 H 2 CrO 4 LiAlH 4 ; H 2 O PRIMARY ALCOHOLS TBSCl, NEt 3 (protection) H 3 C OTBS HF/pyr or Bu 4 N + F - (deprotection) H 3 C OTBS OR O H 3 C NaBH 4 , EtOH H 3 C Br or CrO 3 , H 2 O or K 2 Cr 2 O 7 , H 2 SO 4 (aq) R = H, alkyl A special case: dihydroxylation: H 3 C OsO 4 (cat) , NMO , H 2 O H 3 C OH OH (±) (not good rxn) don't use NaH PBr 3 pyridine
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OH H 3 C CH 3 I CH 3 O H 2 O, heat (S N 1) CH 3 MgBr; H 2 O H 3 O + 1) Hg(OAc) 2 2) NaBH 4 H 3 C CH 3 TsCl , pyridine (deprotonate) H 3 C CH 3 I H 3 C H 3 C CH 3 CH 3 CH 3 CH 3 NaOH (S N 2) H 3 C CH 3 CH 3 CH 3 CH 3 (±) (±) (±) H 3 C CH 3 Cl H 3 C CH 3 OMe H 3 C CH 3 OTs H •(pyridine) 2 DMP (mildest) NaH, MeI (S N 2) 2 SO 4 , MeOH (S N 1, gives racemic product) SOCl 2 , pyridine CH 3 O H 3 C H 3 C CH 3 O H O H 3 C CH 3 H 3 C CH 3 H 3 C 1) BH 3 2) H 2 O 2 /NaOH (±) NaBH 4 , EtOH or LiAlH 4 ; H 2 O SECONDARY ALCOHOLS (S N 1) TBSCl, NEt 3 (protection) HF/pyr or Bu 4 N F (deprotection) OTBS H 3 C CH 3
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This note was uploaded on 04/09/2008 for the course CHEM 20 taught by Professor Shair during the Spring '08 term at Harvard.

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reaction_review - ALKENES Br H2 (D2) Lindlar's cat Pd / C /...

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