Diastereoselective synthesis of β-amino-α-hydroxy phosphonates via oxazaborolidine catalyzed reduction of β-phthalimido-α-keto phosphonates
Reduction of β-phthalimido-α-keto phosphonates, obtained through an Arbuzov reaction between the appropriate acid chloride and triethyl phosphite, with boranes and oxazaborolidine as catalyst, afforded β-phthalimido-α-hydroxy phosphonates in good yields and high diastereoselectivity. Deprotection of...
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| Published in | Tetrahedron letters Vol. 40; no. 43; pp. 7705 - 7708 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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22.10.1999
Elsevier |
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| Abstract | Reduction of β-phthalimido-α-keto phosphonates, obtained through an Arbuzov reaction between the appropriate acid chloride and triethyl phosphite, with boranes and oxazaborolidine as catalyst, afforded β-phthalimido-α-hydroxy phosphonates in good yields and high diastereoselectivity. Deprotection of the amino group gave the title compounds.
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| AbstractList | Reduction of beta-phthalimido-alpha-keto phosphonates, obtained through an Arbuzov reaction between the appropriate acid chloride and triethyl phosphite, with boranes and oxazaborolidine as catalyst, afforded beta-phthalimido-a-hydroxy phosphonates in good yields and high diastereoselectivity. Deprotection of the amino group gave the title compounds. (C) 1999 Elsevier Science Ltd. All rights reserved. Reduction of β-phthalimido-α-keto phosphonates, obtained through an Arbuzov reaction between the appropriate acid chloride and triethyl phosphite, with boranes and oxazaborolidine as catalyst, afforded β-phthalimido-α-hydroxy phosphonates in good yields and high diastereoselectivity. Deprotection of the amino group gave the title compounds. Graphic |
| Author | Zanirato, Vinicio De Risi, Carmela Bergamini, Paola Marchetti, Paolo Pollini, Gian P. Benetti, Simonetta Barco, Achille |
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| Cites_doi | 10.1038/184901b0 10.1016/S0960-894X(96)00545-8 10.1016/S0021-9258(19)44215-4 10.1002/jlac.1995199511276 10.1021/jm00022a022 10.1016/0040-4020(96)00143-3 10.1016/S0957-4166(00)80325-0 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO;2-Z |
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Part 31 - Reduction of carbonyl compounds with chiral oxazaborolidine catalysts: A new paradigm for enantioselective catalysis and a powerful new synthetic method publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Corey, EJ – volume: 38 start-page: 4557 year: 1995 ident: WOS:A1995TD46600022 article-title: ALPHA-HYDROXY PHOSPHINYL-BASED INHIBITORS OF HUMAN RENIN publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: PATEL, DV – volume: 6 start-page: 2989 year: 1996 ident: WOS:A1996VZ84600016 article-title: Stereo selective synthesis of 2-amino-1-hydroxy-3-phenylpropylphosphonic acid publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS contributor: fullname: Zygmunt, J – volume: 5 start-page: 973 year: 1973 ident: WOS:000083043300027.2 publication-title: ORG SYNTH contributor: fullname: BOSE AK – start-page: 2768 year: 1961 ident: WOS:000083043300027.3 publication-title: CHEM BER contributor: fullname: BOSE AK – volume: 52 start-page: 4719 year: 1996 ident: WOS:A1996UC44300016 article-title: 4-Isopropyl-2-oxazoein-5-one anion as masked umpoled synthon for both formyl and hydroxycarbonyl anions: Generation, reactivity and synthetic applications publication-title: TETRAHEDRON contributor: fullname: Barco, A – volume: 248 start-page: 2257 year: 1973 ident: WOS:A1973P203600056 article-title: PHOSPHONOGLYCAN - MAJOR POLYSACCHARIDE CONSTITUENT OF AMEBA PLASMA-MEMBRANE CONTAINS 2-AMINOETHYLPHOSPHONIC ACID AND 1-HYDROXY-2-AMINOETHYLPHOSPHONIC ACID publication-title: JOURNAL OF BIOLOGICAL CHEMISTRY contributor: fullname: KORN, ED – volume: 184 start-page: 901 year: 1959 ident: WOS:A1959ZQ02200053 article-title: ISOLATION OF 2-AMINOETHANE PHOSPHONIC ACID FROM RUMEN PROTOZOA publication-title: NATURE contributor: fullname: HORIGUCHI, M – volume: 4 start-page: 1401 year: 1993 ident: WOS:A1993LK75500002 article-title: STEREODIVERGENT SYNTHESIS OF BETA-AMINO-ALPHA-HYDROXYPHOSPHONIC ACID-DERIVATIVES BY LEWIS-ACID MEDIATED STEREOSELECTIVE HYDROPHOSPHONYLATION OF ALPHA-AMINO ALDEHYDES publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: YOKOMATSU, T – volume: 184 start-page: 901 year: 1959 ident: 10.1016/S0040-4039(99)01573-7_BIB1 publication-title: Nature doi: 10.1038/184901b0 contributor: fullname: Horiguchi – volume: 6 start-page: 2989 year: 1996 ident: 10.1016/S0040-4039(99)01573-7_BIB4 publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/S0960-894X(96)00545-8 contributor: fullname: Zygmunt – volume: 248 start-page: 2257 year: 1973 ident: 10.1016/S0040-4039(99)01573-7_BIB2 publication-title: J. Biol. Chem. doi: 10.1016/S0021-9258(19)44215-4 contributor: fullname: Korn – start-page: 1963 year: 1995 ident: 10.1016/S0040-4039(99)01573-7_BIB12 publication-title: Liebigs Ann. doi: 10.1002/jlac.1995199511276 contributor: fullname: Meier – volume: 38 start-page: 4557 year: 1995 ident: 10.1016/S0040-4039(99)01573-7_BIB3 publication-title: J. Med. Chem. doi: 10.1021/jm00022a022 contributor: fullname: Patel – volume: 52 start-page: 4719 year: 1996 ident: 10.1016/S0040-4039(99)01573-7_BIB5 publication-title: Tetrahedron doi: 10.1016/0040-4020(96)00143-3 contributor: fullname: Barco – volume: 4 start-page: 1401 year: 1993 ident: 10.1016/S0040-4039(99)01573-7_BIB11 publication-title: Tetrahedron: Asymmetry doi: 10.1016/S0957-4166(00)80325-0 contributor: fullname: Yokomatsu – volume: Coll. Vol. V start-page: 973 year: 1973 ident: 10.1016/S0040-4039(99)01573-7_BIB6 publication-title: Org. Synth. contributor: fullname: Bose – start-page: 2768 year: 1961 ident: 10.1016/S0040-4039(99)01573-7_BIB7 publication-title: Chem. Ber. – volume: 37 start-page: 1986 year: 1998 ident: 10.1016/S0040-4039(99)01573-7_BIB9 publication-title: Angew. Chem., Int. Ed. Engl. doi: 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO;2-Z contributor: fullname: Corey |
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| SubjectTerms | amino acid derivatives amino acids Arbuzov reaction Chemistry Chemistry, Organic phosphonic acid derivatives phosphonic acids Physical Sciences Science & Technology |
| Title | Diastereoselective synthesis of β-amino-α-hydroxy phosphonates via oxazaborolidine catalyzed reduction of β-phthalimido-α-keto phosphonates |
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