Organic Chemistry

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Org. Chem. 1987, 52 , 165 t-Butyldimethylsilyl Ether tBuMe 2Si-OR TBS-OR TBDMS-OR JACS 1972, 94 , 6190 - Stable to base and mild acid - under controlled condition is selective for 1° alcohols t-butyldimethylsilyl triflate tBuMe 2Si-OTf TL 1981, 22 , 3455 - very reactive silylating reagent, will silylate 2° alcohols cleavage: - acid - F- (HF, nBu4NF, CsF, KF) TBSO HO CO2Me HF, CH3CN CO2Me (70%) O OTBS O HO JCS Perkin Trans. 1 1981, 2055 t-Butyldiphenylsilyl Ether tBuPh2Si-OR TBDPS-OR ∑-OR - stable to acid and base - selective for 1° alcohols - Me3Si- and iPr 3Si groups can be selectively removed in the presence of TBS or TBDPS groups.

1988, 18 , 89. - even greater 1,4-selectivity Li + HBEt3 (Super Hydride) - very reactive hydride source - reduces ketones, aldehydes, esters, epoxides and C-X (alkyl halides and sulfonates) O HO Li Et3BH, THF HO HCA 1983, 66 , 760 HO H H HO HO CH 3 OH HO 1) TsCl, pyridine 2) Li Et3BH, THF HCA 1988, 71 , 872 HO H H Boranes Hydroboration H2O 2, NaOH B 2H6 B R R' R B 2H6 R' B R B 2H6 H HO H H H3O + H R B H2O 2, NaOH R R' H H R-CH 2CHO H - BH3 reduces carboxylic acids to 1° alcohols in the presence of esters, nitro and cyano groups.

Li (tBuO)3AlH 4. (iBu)2AlH DIBAL-H 5. Na (MeOCH2CH2O)2AlH2 REDAL OH 48 REDUCTIONS 49 Chem. Rev. 1986, 86, 763 Org. Rxn. 1951, 6, 469. Lithium Aluminium Hydride LiAlH4 (LAH) - very powerful reducing agent - used as a suspension in ether or THF - Reduces carbonyl, carboxylic acids and esters to alcohols - Reduces nitrile, amides and aryl nitro groups to amines - opens epoxides - reduces C-X bonds to C-H - reduces acetylenic alcohols trans-allylic alcohols LAH OH R OH R H2N LAH, THF N H NH 2 H2N (62%) NH 2 N H NH 2 Lindlar/ H2 H2N O N H HO CO 2Me OH LAH, THF, ↑↓ TL 1988, 29 , 2793.

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Advanced organic reactions by Stuart W.


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