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WO2002040573A1 - Binaphtyles optiquement actifs a support solide et procede de preparation de derives d'aminonitrile asymetriques a l'aide de ceux-ci - Google Patents

Binaphtyles optiquement actifs a support solide et procede de preparation de derives d'aminonitrile asymetriques a l'aide de ceux-ci Download PDF

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Publication number
WO2002040573A1
WO2002040573A1 PCT/JP2001/009974 JP0109974W WO0240573A1 WO 2002040573 A1 WO2002040573 A1 WO 2002040573A1 JP 0109974 W JP0109974 W JP 0109974W WO 0240573 A1 WO0240573 A1 WO 0240573A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
optically active
formula
solid
supported
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2001/009974
Other languages
English (en)
Japanese (ja)
Inventor
Masakatsu Shibasaki
Hiroyuki Nogami
Motomu Kanai
Shigeki Matsunaga
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Chemical Corp
Original Assignee
Mitsubishi Rayon Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mitsubishi Rayon Co Ltd filed Critical Mitsubishi Rayon Co Ltd
Priority to AU2002224040A priority Critical patent/AU2002224040A1/en
Priority to JP2002531050A priority patent/JP4091837B2/ja
Publication of WO2002040573A1 publication Critical patent/WO2002040573A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/11—Compounds covalently bound to a solid support

Definitions

  • R 3 is a methyl group, a methoxymethyl group, a benzyloxymethyl group, a t-butyl group, a benzyl group, a trimethylsilyl group, a t-butyldimethylsilyl group, or a tetrahydrofuranyl group. More preferably, R 3 represents a methoxymethyl group, and z represents 3.
  • the method for introducing a chloromethyl group into the polymer is not particularly limited, but a method using chloromethyl methyl ether and a Lewis acid such as aluminum chloride, or a method using formaldehyde and hydrochloric acid is used.
  • A— is polystyrene derived from J anda J e 1 TM -C1 resin
  • w l
  • the polymer of A— for example, a chloromethylstyrene′divinylbenzene copolymer Merrifile 1d resin manufactured by Kokusan Kagaku Co., Ltd. Chloromethyl PS force S is used. Also, chloromethylstyrene '1,4-bis (4-vinylphenoxy) butane copolymer JanddaJe1 TM -C1 manufactured by Aldrich Co., Ltd. is used.
  • the terminal phosphonium salt resin represented by the formula (5) is subjected to a Wittig reaction using the compound represented by the formula (17) and a base to obtain a compound represented by the formula (21) supported on a solid phase.
  • a compound represented by the formula (30) supported on a solid phase is obtained by a Deutsch reaction using the compound represented by the formula (17) and a base with respect to the terminal phosphonium salt resin represented by the formula (29) .
  • the base is lithium bis (trimethylsilyl) amide, sodium bis (trimethylsilyl) amide, lithium bis (trimethylsilyl) amide, n-butyllithium, sec-butyllithium, Means using t-butyl lithium or the like is selected.
  • the compound (37) obtained by the above etherification was reacted in a methylene chloride solvent at room temperature for 4 hours in the presence of imidazole (4 equivalents), triphenylphosphine (4 equivalents) and iodine (4 equivalents). .
  • the obtained resin was subjected to suction filtration, washed successively with a large amount of methylene chloride, methanol and dimethyl ether, and then dried in vacuum at 50 ° C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne des binaphtyles optiquement actifs à support solide, un procédé de préparation desdits binaphtyles ou d'intermédiaires de ceux-ci, et un procédé efficace de préparation d'aminonitriles asymétriques à l'aide de ceux-ci. Les binaphtyles optiquement actifs à support solide sont représentés par la formule générale (1) ou (1'), et des aminonitriles asymétriques peuvent être préparés à partir d'imines et de cyanure de triméthyle et à l'aide desdits binaphtyles, R1 étant phényle ou un autre élément semblable, R2 étant hydrogène ou un autre élément semblable, R3 étant hydrogène ou un autre élément semblable, A- représentant un polymère, et -B- représentant un alcoylène éventuellement substitué ou un autre élément semblable.
PCT/JP2001/009974 2000-11-17 2001-11-15 Binaphtyles optiquement actifs a support solide et procede de preparation de derives d'aminonitrile asymetriques a l'aide de ceux-ci Ceased WO2002040573A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2002224040A AU2002224040A1 (en) 2000-11-17 2001-11-15 Solid-supported optically active binaphthyls and process for preparing asymmetric amino nitrile derivatives with the same
JP2002531050A JP4091837B2 (ja) 2000-11-17 2001-11-15 固相担持光学活性ビナフチルおよび固相担持光学活性ビナフチルを用いた不斉アミノニトリル誘導体の製造法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2000351900 2000-11-17
JP2000-351900 2000-11-17

Publications (1)

Publication Number Publication Date
WO2002040573A1 true WO2002040573A1 (fr) 2002-05-23

Family

ID=18824871

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2001/009974 Ceased WO2002040573A1 (fr) 2000-11-17 2001-11-15 Binaphtyles optiquement actifs a support solide et procede de preparation de derives d'aminonitrile asymetriques a l'aide de ceux-ci

Country Status (3)

Country Link
JP (1) JP4091837B2 (fr)
AU (1) AU2002224040A1 (fr)
WO (1) WO2002040573A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998012202A1 (fr) * 1996-09-20 1998-03-26 Oxford Asymmetry International Plc. Ligands phosphiniques
JPH11147890A (ja) * 1997-11-14 1999-06-02 Nissan Chem Ind Ltd 固相担持光学活性ホスフィン
WO1999062855A1 (fr) * 1998-05-29 1999-12-09 E.I. Du Pont De Nemours And Company Hydroformylation d'olefines avec utilisation de ligands di(phosphores) supportes
JP2000053618A (ja) * 1998-08-04 2000-02-22 Sumitomo Chem Co Ltd 光学活性ベンジルアミン類の製造法
JP2000191677A (ja) * 1998-12-28 2000-07-11 Nissan Chem Ind Ltd 光学活性ビナフチル化合物及び該化合物を用いる光学活性シアノヒドリン化合物の製造法
JP2001348392A (ja) * 2000-06-05 2001-12-18 Mitsubishi Rayon Co Ltd 不斉合成触媒用組成物を用いた不斉シアノシリル化物の製造法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998012202A1 (fr) * 1996-09-20 1998-03-26 Oxford Asymmetry International Plc. Ligands phosphiniques
JPH11147890A (ja) * 1997-11-14 1999-06-02 Nissan Chem Ind Ltd 固相担持光学活性ホスフィン
WO1999062855A1 (fr) * 1998-05-29 1999-12-09 E.I. Du Pont De Nemours And Company Hydroformylation d'olefines avec utilisation de ligands di(phosphores) supportes
JP2000053618A (ja) * 1998-08-04 2000-02-22 Sumitomo Chem Co Ltd 光学活性ベンジルアミン類の製造法
JP2000191677A (ja) * 1998-12-28 2000-07-11 Nissan Chem Ind Ltd 光学活性ビナフチル化合物及び該化合物を用いる光学活性シアノヒドリン化合物の製造法
JP2001348392A (ja) * 2000-06-05 2001-12-18 Mitsubishi Rayon Co Ltd 不斉合成触媒用組成物を用いた不斉シアノシリル化物の製造法

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DANIEL J. BAYSTON: "Preparation and use of a polymer supported BINAP hydrogenation catalyst", J. ORG. CHEM., vol. 63, no. 9, 1998, pages 3137 - 3140, XP002908822 *
HIROYUKI NOGAMI ET AL.: "Enantioselective strecker-type reaction promoted by polymer-supported bifuctional catalyst", TETRAHEDRON LETT., vol. 42, no. 2, 2001, pages 279 - 283, XP002908823 *
MASAHIRO TAKAMURA ET AL.: "A catalytic asymmetric strecker-type reation: interesting reactivity difference between TMSCN and HCN", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 39, no. 9, 2000, pages 1650 - 1652, XP002908821 *

Also Published As

Publication number Publication date
JPWO2002040573A1 (ja) 2004-03-25
JP4091837B2 (ja) 2008-05-28
AU2002224040A1 (en) 2002-05-27

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