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Kocienski, Protecting Groups, Georg Thieme Verlag, 1994 1. 2 3. 4. Hydroxyl groups Ketones and aldehydes Amines Carboxylic Acids - Protect functional groups which may be incompatible with a set of reaction conditions - 2 step process- must be efficient - Selectivity a. selective protection b. selective deprotection Hydroxyl Protecting Groups Ethers Methyl ethers R-OH → R-OMe Formation: Cleavage: - difficult to remove except for on phenols CH2N2, silica or HBF4 NaH, MeI, THF AlBr3, EtSH PhSe Ph2P Me3SiI OMe O OH O AlBr3, EtSH TL 1987, 28 , 3659 O O OBz Methoxymethyl ether MOM R-OH → R-OCH2OMe OBz stable to base and mild acid Formation: - MeOCH2Cl, NaH, THF - MeOCH2Cl, CH2Cl2, iPr2EtN Cleavage - Me2BBr2 TL 1983, 24 , 3969 PROTECTING GROUPS Methoxyethoxymethyl ethers (MEM) R-OH → R-OCH2OCH2CH2OMe stable to base and mild acid Formation: - MeOCH2CH2OCH2Cl, NaH, THF - MeOCH2CH2OCH2Cl, CH2Cl2, iPr2EtN Cleavage - Lewis acids such as ZnBr2, TiCl4, Me2BBr2 TL 1976, 809 S B Cl MEM-O HO S C5H11 O-Si(Ph)2tBu O C5H11 TL 1983, 24 , 3965, 3969 O O-Si(Ph)2tBu - can also be cleaved in the presence of THP ethers Methyl Thiomethyl Ethers (MTM) R-OH → R-OCH2SMe Stable to base and mild acid Formation: - MeSCH2Cl, NaH, THF Cleavage: - HgCl2, CH3CN/H2O - AgNO3, THF, H2O, base Benzyloxymethyl Ethers (BOM) R-OH → R-OCH2OCH2Ph Stable to acid and base Formation: - PhOCH2CH2Cl, CH2Cl2, iPr2EtN Cleavage: - H2/ PtO2 - Na/ NH3, EtOH Tetrahydropyranyl Ether R-OH (THP) O H + , PhH Formation Cleavage: R O O Stable to base, acid labile - DHP (dihydropyran), pTSA, PhH - AcOH, THF, H2O - Amberlyst H-15, MeOH Ethoxyethyl ethers (EE) JACS 1979, 101 , 7104; JACS 1974, 96 , 4745.

Alkyl Borohydrides Selectrides M + HB 3 M + = Li (L-selectride) K (K-selectride) LS-selectride Li + HB 3 - hindered reducing agent increased selectivity based on steric considerations CO 2H O CO 2H OH L-selectride THF JACS 1971, 93, 1491 R R HO HO OH OH REDUCTIONS 45 - selective 1,4-reductions of α,β-unsaturated carbonyl cmpds. JOC 1975, 40 , 146; JOC 1976, 41 , 2194 O O K-selectride, THF (99%) - 1,4-reduction generates an enolate which can be subsequently alkylated. O O a) K-selectride, THF b) Br K+ HBPh3 Syn.

Bull. 1981, 29 , 1159; Chem. Ber. 1984, 117 , 856. Ar-NO2 → Ar-NH2 Ar-NO → Ar- NH2 R2C=N-OH → R2CH-NH2 NaBH4 / TiCl 4 Synthesis 1980, 695. R-COOH → R-CH2-OH R-COOR' → R-CH2-OH R-CN → R-CH2-NH2 R-CONH2 → R-CH2-NH2 R2C=N-OH → R2CH-NH2 R-SO2-R' → R-S-R' NaBH4 / CeCl 3 Luche Reduction reduced α,β-unsaturated ketones in a 1,2-fashion OH NaBH 4/ CeCl3 R R NaBH 4 R R O OH O R + R R R R R R H R JCSCC 1978, 601 JACS 1978, 100 , 2226 O OH CO 2Me NaBH 4/ CeCl3 C 5H11 CO 2Me MeOH C 5H11 OH OH - selective reduction of ketones in the presence of aldehydes.

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