Journal ArticleDOI
First catalytic asymmetric hydrophosphonylation of cyclic imines: Highly efficient enantioselective approach to a 4-thiazolidinylphosphonate via chiral titanium and lanthanoid catalysts
TLDR
A highly efficient enantioselective de novo approach to the pharmaceutically interesting 4-thiazolidinylphosphonate 2 using either titanium or lanthanoid chiral catalysts, which gives excellent enantiomeric purities and high chemical yields.About:
This article is published in Tetrahedron Letters.The article was published on 1996-12-23. It has received 60 citations till now. The article focuses on the topics: Enantioselective synthesis & Imine.read more
Citations
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Journal ArticleDOI
Catalytic enantioselective addition to imines.
Shu Kobayashi,Haruro Ishitani +1 more
TL;DR: Shū Kobayashi was born in 1959 in Tokyo, Japan and studied chemistry at the University of Tokyo and received his Ph.D. in 1988 (Professor T. Mukaiyama), and received the first Springer Award in Organometallic Chemistry in 1997.
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Lanthanide complexes in multifunctional asymmetric catalysis.
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Asymmetric Catalysis with Heterobimetallic Compounds
TL;DR: In this paper, the authors describe the development of rare-earth-alkali metal complexes such as LnM3tris(binaphthoxide) complexes (LnMB, Ln = rare earth metal, M = alkali metal), which are readily prepared from corresponding rare earth trichlorides or rare earth isopropoxides, and their application to catalytic asymmetric synthesis.
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Thiourea-catalyzed enantioselective hydrophosphonylation of imines: practical access to enantiomerically enriched alpha-amino phosphonic acids.
Guy Joly,Eric N. Jacobsen +1 more
TL;DR: Chiral thiourea 1b catalyzes the highly enantioselective hydrophosphonylation of a wide range of N-benzyl imines, providing access to free alpha-amino phosphonic acids in highly enantioenriched form.
References
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Chiral titanium complexes for enantioselective addition of nucleophiles to carbonyl groups
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The First Heterobimetallic Multifunctional Asymmetric Catalyst
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On the Mechanisms of Enantioselective Reactions Using α,α,α′,α′ -Tetraaryl-1,3-dioxolane-4,5-dimethanol(TADDOL)-Derived Titanates: Differences between C2- and C1-symmetrical TADDOLs – facts, implications and generalizations†
TL;DR: In this article, it was shown that a single chiral titanate is involved in the product-forming step, and that the bulky TADDOLate ligand renders the Ti-center catalytically more active than that of (i-PrO)4Ti, due to fast dynamics of ligand exchange on the sterically hindered Ti center.
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Catalytic Asymmetric Synthesis of .alpha.-Amino Phosphonates Using Lanthanoid-Potassium-BINOL Complexes
TL;DR: The authors report here the first example of a catalytic asymmetric hydrophosphonylation to imines using lanthanoids-potassium-BINOL heterobimetallic complexes (LnPB, Ln = lanthanoid metal), which gives optically active {alpha}-amino phosphonates in modest to high enantiometric excess.