Efficient synthesis of the four diastereomers of phosphothreonine from lactalhehyde

[1]  E. Bandini,et al.  Diastereofacial Selectivity in the Reaction of Chiral N-Trimethylsilyl Imines with Ester Enolates: Preparation of trans-Azetidin-2-ones in High Stereocontrolled Fashion. , 1996 .

[2]  M. Shibasaki,et al.  Catalytic Asymmetric Synthesis of .alpha.-Amino Phosphonates Using Lanthanoid-Potassium-BINOL Complexes , 1995 .

[3]  E. Bandini,et al.  Silicon directed asymmetric synthesis of (1R, 2S)-(−)-(1,2-Epoxypropyl)phosphonic acid (fosfomycin) from (S)-lactaldehyde , 1995 .

[4]  R. Noyori,et al.  Asymmetric synthesis of α-amino β-hydroxy phosphonic acids via BINAP-ruthenium catalyzed hydrogenation , 1995 .

[5]  P. Galletti,et al.  Acyclic stereocontrol in the addition of trimethylsilyl cyanide to N-substituted imines of (2S)-lactic aldehyde , 1995 .

[6]  C. Rücker,et al.  The Triisopropylsilyl Group in Organic Chemistry: Just a Protective Group, or More? , 1995 .

[7]  E. Bandini,et al.  Stereoselective Synthesis of α,β-Disilyloxy Phosphonates by Stereoselective Phosphonylation of α-Silyloxyaldehydes , 1995 .

[8]  B. W. Gung,et al.  Transition State of the Silicon-Directed Aldol Reaction: An ab Initio Molecular Orbital Study , 1995 .

[9]  E. Bandini,et al.  β-Lactams from ester enolates and N-TMSimines: Enantioselective synthesis of (6R, 7S)-1β-3-dimethyl-3-isocephem , 1995 .

[10]  A. Bongini,et al.  Studies on N-metallo imines: dependence of chemical shift of the 13C iminic carbon from the nature of the nitrogen substituent , 1995 .

[11]  O. García-Barradas,et al.  HIGHLY ENANTIOSELECTIVE SYNTHESIS OF (R)- AND (S)-2-AMINO-5-PHOSPHONOPENTANOIC ACIDS (R)- AND (S)-AP5 VIA MODIFIED SEEBACH IMIDAZOLIDINONES , 1995 .

[12]  R. Noyori,et al.  Asymmetric Hydrogenation of .beta.-Keto Phosphonates: A Practical Way to Fosfomycin , 1995 .

[13]  J. Luche,et al.  RADICAL VERSUS POLAR MECHANISMS. THE SONOCHEMICAL ADDITION OF PHOSPHONATE ESTERS TO IMINES , 1995 .

[14]  G. Sello,et al.  Alkylation of chiral phosphonoglycine equivalents: Asymmetric synthesis of diethyl α-amino-α-alkyl-phosphonates , 1995 .

[15]  K. Koeller,et al.  Reactions of Chiral Phosphorous Acid Diamides: The Asymmetric Synthesis of Chiral .alpha.-Hydroxy Phosphonamides, Phosphonates, and Phosphonic Acids , 1995 .

[16]  T. Yamagishi,et al.  Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of vinylphosphonates. An application to the stereocontrolled synthesis of (4S,5S)-4-diethylphosphono-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane , 1995 .

[17]  S. Shibuya,et al.  Stereoselective Synthesis of .beta.-Oxygenated .alpha.-Hydroxyphosphonates by Lewis Acid-Mediated Stereoselective Hydrophosphonylation of .alpha.-Benzyloxy Aldehydes. An Application to the Synthesis of Phosphonic Acid Analogs of Oxyamino Acids , 1994 .

[18]  W. Malachowski,et al.  The Chemistry of Phosphapeptides: Formation of Functionalized Phosphonochloridates under Mild Conditions and Their Reaction with Alcohols and Amines , 1994 .

[19]  K. Nishio,et al.  Facile and Highly Stereoselective Synthesis of Homoallylic Alcohols Using Organosilicon Intermediates , 1994 .

[20]  Carol M. Taylor,et al.  Asymmetric Synthesis of .alpha.-Aminophosphonates via Diastereoselective Addition of Lithium Diethyl Phosphite to Chelating Imines , 1994 .

[21]  T. Gajda.  Enantioselective synthesis of diethyl 1-hydroxyalkylphosphonates via oxazaborolidine catalyzed borane reduction of diethyl α-ketophosphonates , 1994 .

[22]  S. Denmark,et al.  Chemistry of Enoxysilacyclobutanes - Highly Selective Uncatalyzed Aldol Additions , 1994 .

[23]  N. Rath,et al.  The enantioselective addition of dialkylphosphites to aldehydes: Catalysis by a lanthanum binaphthoxide complex , 1994 .

[24]  E. Karran,et al.  Synthesis of novel N-phosphonoalkyl dipeptide inhibitors of human collagenase. , 1994, Journal of medicinal chemistry.

[25]  K. Janda.  Catalytic antibodies and enzyme inhibitors , 1994 .

[26]  E. Bandini,et al.  Synthesis of carbapenems via metalloimines-ester enolates condensation: a new synthesis of (+)-1β-methyl PS-5 , 1993 .

[27]  R. Neidlein,et al.  Synthesen von α‐Aminophosphonsäuren aus N‐Ethoxyiminium‐Salzen, II , 1993 .

[28]  S. Evans,et al.  Diastereoselective condensation of oxazaphosphites with aliphatic and aromatic aldehydes , 1993 .

[29]  T. Kee,et al.  Synthetic, stereochemical and mechanistic studies on the asymmetric phosphonylation of aldehydes via 2-triorganosiloxy-1,3,2-oxazaphospholidines , 1993 .

[30]  Fernando Bernardi,et al.  Theoretical study of the aldol condensation with imine-type electrophiles , 1993 .

[31]  T. Nakai,et al.  Control of chelation/nonchelation stereoselections in lanthanide-catalysed aldol reactions , 1993 .

[32]  T. Reilly,et al.  Synthesis of phosphonopeptides as thrombin inhibitors , 1992 .

[33]  A. Myers,et al.  Silicon-directed aldol reactions. Rate acceleration by small rings , 1992 .

[34]  B. Stowasser,et al.  C2-symmetric phosphinic acid inhibitors of HIV protease , 1992 .

[35]  M. Reetz,et al.  A rapid injection NMR study of the chelation controlled Mukaiyama aldol addition: TiCl4 versus LiClO4 as the Lewis acid , 1992 .

[36]  A. Myers,et al.  Silicon-directed aldol condensation. Evidence for a pseudorotational mechanism , 1992 .

[37]  S. Frye,et al.  Chelates as intermediates in nucleophilic additions to alkoxy ketones according to Cram's rule (cyclic model) , 1992 .

[38]  S. Denmark,et al.  Asymmetric electrophilic amination of chiral phosphorus-stabilized anions , 1992 .

[39]  C. Yuan,et al.  Studies on Organophosphorus Compounds; LXIII. A New and Facile Synthetic Route to Protected Phosphonodipeptides: A Backbone for the Formation of Oligophosphonopeptides , 1992 .

[40]  F. Hammerschmidt.  Addition von Dialkylphosphiten und Dialkyl(trimethylsilyl)phosphiten an 2-(Benzyloxy)propanal: Darstellung aller vier stereoisomeren (1,2-Dihydroxy-[1-2H1]propyl)phosphonsäuren aus chiralen Lactaten , 1991 .

[41]  H. Kaehlig,et al.  Biosynthesis of natural products with a phosphorus-carbon bond. 7. Synthesis of [1,1-2H2]-, [2,2-2H2]-, (R)- and (S)-[1-2H1](2-hydroxyethyl)phosphonic acid and (R,S)-[1-2H1](1,2-dihydroxyethyl)phosphonic acid and incorporation studies into fosfomycin in Streptomyces fradiae , 1991 .

[42]  B. Johnston,et al.  A convenient synthesis of both enantiomers of seudenol and their conversion to 1-methyl-2-cyclohexen-1-Ol (MCOL) , 1991 .

[43]  K. Bayer,et al.  Das Oxiran-Sauerstoff-Atom des Fosfomycins entstammt nicht dem Luft-Sauerstoff , 1990 .

[44]  J. Cadogan,et al.  Synthesis of organophosphorus compounds via silyl esters of phosphorous acids , 1990 .

[45]  S. Hanessian,et al.  The asymmetric synthesis of α-chloro α-alkyl and α-methyl α-alkyl phosphonic acids of high enantiomeric purity. , 1990 .

[46]  H. Völlenkle,et al.  Absolute Konfiguration der (2‐Amino‐1‐hydroxyethyl)phosphonsäure aus Acanthamoeba castellanii (Neff) ‐ Darstellung der Phosphonsäure‐Analoga von (+)‐ und (‐)‐Serin , 1989 .

[47]  D. Seebach,et al.  Elektrochemische Decarboxylierung von L.‐Threonin‐ und Oligopeptid‐Derivaten unter Bildung von N‐Acyl‐N, O‐acetalen: Herstellung von Oligopeptiden mit Carboxamid‐oder Phosphonat‐C‐Terminus , 1989 .

[48]  Yitzhak Apeloig,et al.  The chemistry of organic silicon compounds , 1989 .

[49]  L. Wozniak,et al.  Silyl esters of phosphorous—common intermediates in synthesis , 1989 .

[50]  T. Jones,et al.  Enantioselective construction of heterocycles. Synthesis of (R,R)-solenopsin B , 1988 .

[51]  P. Bartlett,et al.  Diastereoselectivity in the alkylation of chiral 2-aminomethyl-1,3,2-dioxaphosphorinane 2-oxides , 1987 .

[52]  P. Bartlett,et al.  Phosphorus amino acid analogues as inhibitors of leucine aminopeptidase. , 1987, Journal of medicinal chemistry.

[53]  D. Redmore,et al.  OPTICALLY ACTIVE 1-AMINOALKYLPHOSPHONIC ACIDS , 1987 .

[54]  U. Schöllkopf,et al.  Asymmetrische Synthese von α-Aminophosphonsäuren. III: Asymmetrische Synthese von (S)-(1-Aminoalkyl)phosphonsäure-diethylestern unter Verwendung von (+)-Campher als chiralem Hilfsreagens , 1987 .

[55]  M. Reetz,et al.  Non-chelation-controlled nucleophilic addition to chiral α-siloxyketones , 1986 .

[56]  John A. Robinson,et al.  Novel renin inhibitors: synthesis of aminostatine and comparison with statine-containing analogues , 1986 .

[57]  A. Vasella,et al.  Nucleophilic Additions to N-Glycosylnitrones. Asymmetric Synthesis of α-Aminophosphonic Acids†‡ , 1985 .

[58]  C. D. Campbell,et al.  1-Aminoalkylphosphonous acids. Part 1. Isosteres of the protein amino acids , 1985 .

[59]  M. Reetz,et al.  Chelation or Non‐Chelation Control in Stereoselective Reactions of Titanium Reagents with Chiral Alkoxycarbonyl Compounds , 1983 .

[60]  J. Tronchet,et al.  Structural analysis of 3-C-phosphonates, -phosphinates, and -phosphine oxides of branched-chain sugars , 1983 .

[61]  M. Sekine,et al.  A New Type of P–C and C–C Bond Cleavage Reactions in α-Trimethylsilyloxy-β-oxo Phosphonates and α-Ethoxy-β-oxo Phosphonates. The Synthesis of Unsymmetrical α-Hydroxy Ketones Utilizing 1:1 Carbonyl Adducts of Diethyl Trimethylsilyl Phosphite with Benzaldehyde , 1982 .

[62]  O. Mitsunobu.  The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products , 1981 .

[63]  M. Sekine,et al.  Silyl phosphites. 15. Reactions of silyl phosphites with .alpha.-halo carbonyl compounds. Elucidation of the mechanism of the Perkow reaction and related reactions with confirmed experiments , 1981 .

[64]  Davidr . Evans,et al.  New Silicon-Phosphorus Reagents in Organic Synthesis. Carbonyl and Conjugate Addition Reactions of Silicon Phosphite Esters and Related Systems , 1978 .