Mukaiyama aldol addition

Mukaiyama aldol addition

Clarify original Mukaiyama aldol report

← Previous revision Revision as of 05:00, 19 April 2026
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In [[organic chemistry]], the '''Mukaiyama aldol addition''' is an [[organic reaction]] and a type of [[aldol reaction]] between a [[silyl enol ether]] ({{chem2|R2C\dCR\sO\sSi(CH3)3}}) and an [[aldehyde]] ({{chem2|R\sCH\dO}}) or [[formate]] ({{chem2|R\sO\sCH\dO}}).{{cite journal | last1 = Mukaiyama | first1 = T. | last2 = Kobayashi | first2 = S. | year = 1994 | title = Tin(II) Enolates in the Aldol, Michael, and Related Reactions| journal = [[Org. React.]] | volume = 46 | page = 1 | doi = 10.1002/0471264180.or046.01 | isbn = 0471264180 }} The reaction was discovered by [[Teruaki Mukaiyama]] in 1973.''New aldol type reaction'' Teruaki Mukaiyama, Koichi Narasaka and Kazuo Banno [[Chemistry Letters]] Vol.2 ('''1973'''), No.9 pp. 1011–1014 {{doi|10.1246/cl.1973.1011}} His choice of reactants allows for a crossed aldol reaction between an aldehyde and a [[ketone]] ({{chem2|>C\dO}}), or a different aldehyde without [[self-condensation]] of the aldehyde. For this reason the reaction is used extensively in [[organic synthesis]].
In [[organic chemistry]], the '''Mukaiyama aldol addition''' is an [[organic reaction]] and a type of [[aldol reaction]] between a [[silyl enol ether]] ({{chem2|R2C\dCR\sO\sSi(CH3)3}}) and an [[aldehyde]] ({{chem2|R\sCH\dO}}) or [[formate]] ({{chem2|R\sO\sCH\dO}}).{{cite journal | last1 = Mukaiyama | first1 = T. | last2 = Kobayashi | first2 = S. | year = 1994 | title = Tin(II) Enolates in the Aldol, Michael, and Related Reactions| journal = [[Org. React.]] | volume = 46 | page = 1 | doi = 10.1002/0471264180.or046.01 | isbn = 0471264180 }} The reaction was reported in 1973 by [[Teruaki Mukaiyama]], Koichi Narasaka and Kazuo Banno from the Laboratory of Organic Chemistry, [[Tokyo Institute of Technology]].{{cite journal |last1=Mukaiyama |first1=Teruaki |last2=Narasaka |first2=Koichi |last3=Banno |first3=Kazuo |title=New Aldol Type Reaction |journal=Chemistry Letters |volume=2 |issue=9 |pages=1011-1014 |year=1973 |doi=10.1246/cl.1973.1011}} His choice of reactants allows for a crossed aldol reaction between an aldehyde and a [[ketone]] ({{chem2|>C\dO}}), or a different aldehyde without [[self-condensation]] of the aldehyde. For this reason the reaction is used extensively in [[organic synthesis]].


==General reaction scheme==
==General reaction scheme==