Keiji Maruoka

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTEnantioselective Amino Acid Synthesis by Chiral Phase-Transfer CatalysisKeiji Maruoka and Takashi OoiView Author Information Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan Cite this: Chem. Rev. 2003, 103, 8, 3013–3028Publication Date (Web):June 13, 2003Publication History Received16 January 2003Published online13 June 2003Published inissue 1 August 2003https://pubs.acs.org/doi/10.1021/cr020020ehttps:

Phase-transfer catalysis has been recognized as a powerful method for establishing practical protocols for organic synthesis, because it offers several advantages, such as operational simplicity, mild reaction conditions, suitability for large-scale synthesis, and the environmentally benign nature of the reaction system. Since the pioneering studies on highly enantioselective alkylations promoted by chiral phase-transfer catalysts, this research field has served as an attractive area for the pur

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAsymmetric hetero-Diels-Alder reaction catalyzed by a chiral organoaluminum reagentKeiji. Maruoka, Takayuki. Itoh, Tadashi. Shirasaka, and Hisashi. YamamotoCite this: J. Am. Chem. Soc. 1988, 110, 1, 310–312Publication Date (Print):January 1, 1988Publication History Published online1 May 2002Published inissue 1 January 1988https://pubs.acs.org/doi/10.1021/ja00209a061https://doi.org/10.1021/ja00209a061research-articleACS PublicationsRequest reuse permiss

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTOrganoaluminum-promoted Beckmann rearrangement of oxime sulfonatesKeiji Maruoka, Tohru Miyazaki, Mamoru Ando, Yasushi Matsumura, Soichi Sakane, Kazunobu Hattori, and Hisashi YamamotoCite this: J. Am. Chem. Soc. 1983, 105, 9, 2831–2843Publication Date (Print):May 1, 1983Publication History Published online1 May 2002Published inissue 1 May 1983https://pubs.acs.org/doi/10.1021/ja00347a052https://doi.org/10.1021/ja00347a052research-articleACS PublicationsR

This review article outlines the recent practical aspects of asymmetric phase-transfer catalysis including (1) asymmetric alkylation of glycine and α-substituted amino acid derivatives as well as other substrates, (2) asymmetric Michael addition, (3) asymmetric aldol reaction, (4) asymmetric Mannich reaction, (5) asymmetric epoxidation, (6) asymmetric aziridination, (7) and the asymmetric Strecker reaction.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAmphiphilic reactions by means of exceptionally bulky organoaluminum reagents. Rational approach for obtaining unusual equatorial, anti-Cram, and 1,4 selectivity in carbonyl alkylationKeiji. Maruoka, Takayuki. Itoh, Minoru. Sakurai, Katsumasa. Nonoshita, and Hisashi. YamamotoCite this: J. Am. Chem. Soc. 1988, 110, 11, 3588–3597Publication Date (Print):May 1, 1988Publication History Published online1 May 2002Published inissue 1 May 1988https://pubs.acs.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTChiral helical Lewis acids for asymmetric Diels-Alder catalystsKeiji Maruoka, Noriaki Murase, and Hisashi YamamotoCite this: J. Org. Chem. 1993, 58, 11, 2938–2939Publication Date (Print):May 1, 1993Publication History Published online1 May 2002Published inissue 1 May 1993https://pubs.acs.org/doi/10.1021/jo00063a006https://doi.org/10.1021/jo00063a006research-articleACS PublicationsRequest reuse permissionsArticle Views878Altmetric-Citations153LEARN ABOU

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTMethylaluminum bis(2,6-di-tert-butyl-4-alkylphenoxide). A new reagent for obtaining unusual equatorial and anti-Cram selectivity in carbonyl alkylationKeiji Maruoka, Takayuki Itoh, and Hisashi YamamotoCite this: J. Am. Chem. Soc. 1985, 107, 15, 4573–4576Publication Date (Print):July 1, 1985Publication History Published online1 May 2002Published inissue 1 July 1985https://pubs.acs.org/doi/10.1021/ja00301a048https://doi.org/10.1021/ja00301a048research-ar

Oompa loompa: The title reaction has been accomplished with high stereoselectivity by use of an axially chiral dicarboxylic acid (see scheme). Employment of vinylogous aza-enamines as novel dipolarophiles was also implemented to establish a new concept of the inverse-electron-demand umpolung 1,3-dipolar cycloaddition. Bz=benzoyl, EDG=electron-donating group. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not cop

Abstract Die Phasentransferkatalyse bildet eine effiziente Grundlage zur Einführung praktischer Methoden in die organische Synthese, denn sie bietet mehrere Vorteile wie einfache Handhabung, milde Reaktionsbedingungen, die Eignung für großtechnische Synthesen und ein umweltfreundliches Reaktionssystem. Seit den wegweisenden Arbeiten zu hoch enantioselektiven Alkylierungen mit chiralen Phasentransferkatalysatoren ist dieses Forschungsgebiet im Hinblick auf eine umweltverträgliche, nachhaltige Che

It all adds up: The title reaction was developed for the synthesis of chiral tetrahydroisoquinoline derivatives with a tetrasubstituted carbon center at the C1-position (see scheme, Bz=benzoyl, pybox=2,6-bis(2-oxazolinyl)pyridine). The reaction was facilitated effectively by the co-catalyst system composed of copper(I)/Ph-pybox and an axially chiral dicarboxylic acid.