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WO2006023720A3 - Reactions of enolizable a-amino aldehydes or ketones to form amine - Google Patents

Reactions of enolizable a-amino aldehydes or ketones to form amine Download PDF

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Publication number
WO2006023720A3
WO2006023720A3 PCT/US2005/029542 US2005029542W WO2006023720A3 WO 2006023720 A3 WO2006023720 A3 WO 2006023720A3 US 2005029542 W US2005029542 W US 2005029542W WO 2006023720 A3 WO2006023720 A3 WO 2006023720A3
Authority
WO
WIPO (PCT)
Prior art keywords
diprotectedamino
enolizable
product
ketones
reactions
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/US2005/029542
Other languages
French (fr)
Other versions
WO2006023720A2 (en
Inventor
Carlos F Barbas Iii
Rajeswari Thayumanavan
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.)
Scripps Research Institute
Original Assignee
Scripps Research Institute
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 Scripps Research Institute filed Critical Scripps Research Institute
Publication of WO2006023720A2 publication Critical patent/WO2006023720A2/en
Publication of WO2006023720A3 publication Critical patent/WO2006023720A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/30—Preparation of optical isomers
    • C07C227/32—Preparation of optical isomers by stereospecific synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C223/00—Compounds containing amino and —CHO groups bound to the same carbon skeleton
    • C07C223/02—Compounds containing amino and —CHO groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07B2200/07—Optical isomers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A method for asymmetrically forming a (diprotectedamino)-product having a chiral center and in which one enantiomer is in excess over the other is disclosed. The method comprises reacting an enolizable alpha- (diprotectedamino)-aldehyde or -ketone donor molecule with an excess of an unsaturated acceptor molecule that has one or no hydrogen atoms bonded to a carbon atom alpha to the carbon of the unsaturation. The donor and acceptor molecules are dissolved or dispersed in a liquid solvent and are in the presence of a chiral amine catalyst to form an addition product reaction medium. The reaction medium is maintained for a time sufficient to form an α-(diprotectedamino)-aldehyde or -ketone product having a chiral center formed at a carbon atom bonded to the α-(diprotectedamino) group and in which one enantiomer is in excess over the other.
PCT/US2005/029542 2004-08-20 2005-08-19 Reactions of enolizable a-amino aldehydes or ketones to form amine Ceased WO2006023720A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US60317504P 2004-08-20 2004-08-20
US60/603,175 2004-08-20

Publications (2)

Publication Number Publication Date
WO2006023720A2 WO2006023720A2 (en) 2006-03-02
WO2006023720A3 true WO2006023720A3 (en) 2007-01-11

Family

ID=35968199

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2005/029542 Ceased WO2006023720A2 (en) 2004-08-20 2005-08-19 Reactions of enolizable a-amino aldehydes or ketones to form amine

Country Status (1)

Country Link
WO (1) WO2006023720A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008115116A (en) * 2006-11-06 2008-05-22 Nagoya Institute Of Technology Method for producing α-hydroxy-α-trifluoromethyl-γ-lactam derivative
WO2009039181A2 (en) * 2007-09-17 2009-03-26 State Of Oregon Acting By & Through The State Board Of Higher Education On Behalf Of Or. State Univ. Sulfonamide-based organocatalysts and method for their use

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
THAYUMANAVAN R. ET AL.: "Direct Organocatalytic Asymmetric Aldol Reactions of alpha-Amino Aldehydes: Expedient Syntheses of Highly Enantiomerically Enriched anti-beta-Hydroxy-alpha-amino Acids", ORGANIC LETTERS, vol. 6, no. 20, 2004, pages 3541 - 3544, XP003006244 *

Also Published As

Publication number Publication date
WO2006023720A2 (en) 2006-03-02

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