A Versatile Synthesis of Unsymmetrical 3,3′-Bioxindoles: Stereoselective Mukaiyama Aldol Reactions of 2-Siloxyindoles with Isatins
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چکیده
منابع مشابه
Stereoselective Acetate Aldol Reactions
The stereochemical control of aldol reactions from unsubstituted enolor enolatelike species, what are known as acetate aldol reactions, has been a matter of concern for nearly 30 years [1, 2]. Indeed, pioneering studies soon recognized that the asymmetric installation of a single stereocenter in such aldol reactions was much more demanding than the simultaneous construction of two new stereocen...
متن کاملVinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis
BACKGROUND The diastereoselectivity of a vinylogous Mukaiyama aldol reaction of a series of N-substituted 4-oxy-2-trimethylsilyloxypyrroles with a tartrate-based aldehyde has been explored as a model reaction for castanospermine synthesis. RESULTS The study has revealed that the reaction is sensitive to the nature of the combination of N- and 4-oxy substituents. With a N-PMB or N-Bn and 4-met...
متن کاملMukaiyama Aldol Reactions in Aqueous Media
Mukaiyama aldol reactions in aqueous media have been surveyed. While the original Mukaiyama aldol reactions entailed stoichiometric use of Lewis acids in organic solvents under strictly anhydrous conditions, Mukaiyama aldol reactions in aqueous media are not only suitable for green sustainable chemistry but are found to produce singular phenomena. These findings led to the discovery of a series...
متن کاملStereoselective synthesis of activated 2-arylazetidines via imino-aldol reaction.
A simple and efficient synthetic route to substituted N-sulfinyl and N-sulfonyl azetidines is described involving imino-aldol reaction of ester enolates with racemic and non-racemic aldimines for obtaining β-amino esters as a key step. These β-amino esters on subsequent reduction followed by TsCl/KOH mediated cyclization produced the corresponding racemic and non-racemic azetidines with high yi...
متن کاملA tandem non-aldol aldol Mukaiyama aldol reaction.
[reaction: see text] A new one-pot tandem aldol process is described in which a secondary epoxy silyl ether is converted into the 1,5-bis-silyloxy-3-alkanone in good yield. Thus, treatment of the epoxy silyl ether 8 with TBSOTf and base affords the silyl enol ether 9 via non-aldol aldol rearrangement and addition of benzaldehyde and TBSOTf gives the ketone 10 with 4:1 syn selectivity. The diast...
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2008
ISSN: 0022-3263,1520-6904
DOI: 10.1021/jo801867w