Download PDF by Rizzo C.J.: Advanced Organic Reactions

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By Rizzo C.J.

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NaBH4 reduces ketones and aldehydes LiBH4 reduces ketones, aldehydes, esters and epoxides. THF soluble LiBH4/TMSCl stronger reducing agent. ACIEE 1989, 28, 218. Zn(BH4)2 reduces ketones and aldehydes R4N BH4 organic soluble (CH2Cl2) borohydrides. Synth Commun. 1990, 20, 907 LiEt3BH reduces ketones, aldehydes, esters, epoxides and R-X Li s-Bu3BH reduces ketones, aldehydes, esters and epoxides (hindered borohydride) Na(CN)NH3 reduces iminium ions, ketones and aldehydes Na(AcO)3BH reduces ketones and aldehydes (less reactive) NaBH2S3 reduces ketones and aldehydes REDUCTIONS 41 Sodium Borohydride NaBH4 - reduces aldehydes and ketones to alcohols - does not react with acids, esters, lactones, epoxides or nitriles.

1975, 1045; 1159; 1976, 49; 1977, 575 O + R OH F + N Me O TsO R O + N I- Me Acetates R-OH → R-O2CCH3 - stable to acid and mild base - not compatable with strong base or strong nucleophiles such as organometallic reagents Formation: - acetic anhydride, pyridine - acetyl chloride, pyridine PROTECTING GROUPS Cleavage: - K2CO3, MeOH, reflux KCN, EtOH, reflux NH3, MeOH LiOH, THF, H2O enzymatic hydrolysis (Lipase) OAc 64 Org. Rxns. 1989, 37, 1. OAc Porcine Pancreatic Lipase TL 1988, 30 , 6189 OAc OH (96% ee) Chloroacetates - can be selectively cleaved with Zn dust or thiourea.

1986, 86 , 763. NaBH4 reduces ketones and aldehydes LiBH4 reduces ketones, aldehydes, esters and epoxides. THF soluble LiBH4/TMSCl stronger reducing agent. ACIEE 1989, 28, 218. Zn(BH4)2 reduces ketones and aldehydes R4N BH4 organic soluble (CH2Cl2) borohydrides. Synth Commun. 1990, 20, 907 LiEt3BH reduces ketones, aldehydes, esters, epoxides and R-X Li s-Bu3BH reduces ketones, aldehydes, esters and epoxides (hindered borohydride) Na(CN)NH3 reduces iminium ions, ketones and aldehydes Na(AcO)3BH reduces ketones and aldehydes (less reactive) NaBH2S3 reduces ketones and aldehydes REDUCTIONS 41 Sodium Borohydride NaBH4 - reduces aldehydes and ketones to alcohols - does not react with acids, esters, lactones, epoxides or nitriles.

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Advanced Organic Reactions by Rizzo C.J.


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