syn-Selective dihydroxylation of γ-amino-α,β-unsaturated (Z)-esters from d-serine: stereoselective synthesis of d-iminolyxitol

Jeon, Jongho; Lee, Jong Hyup; Kim, Jungwon; Kim, Young Gyu

doi:10.1016/j.tetasy.2007.10.004

Cited by 12 publications

(6 citation statements)

References 37 publications

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“…Prolonging the reaction time to 120 h afforded a complex reaction mixture (Table 1, Entry 4). Having no success with Sharpless asymmetric dihydroxylation, we employed an Upjohn dihydroxylation 36. Using a catalytic amount of OsO 4 and 2.5 equiv.…”

Section: Resultsmentioning

confidence: 99%

Selective Elaboration of Aminodiols towards Small Ring α‐ and β‐Amino Acid Derivatives that Incorporate an Aziridine, Azetidine, or Epoxide Scaffold

et al. 2016

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The osmium‐catalyzed dihydroxylation of N‐substituted alkyl 2‐(aminomethyl)acrylates resulted in the efficient synthesis of 2‐(aminomethyl)‐2,3‐dihydroxypropanoates in good yields (82–89 %). The resulting aminodiols were elaborated in a selective diversity‐oriented synthesis to produce the corresponding 2‐(aminomethyl)oxirane‐2‐carboxylates, functionalized aziridine‐2‐carboxylates, and azetidine‐3‐carboxylates by using straightforward reactions.

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Section: Resultsmentioning

confidence: 99%

Selective Elaboration of Aminodiols towards Small Ring α‐ and β‐Amino Acid Derivatives that Incorporate an Aziridine, Azetidine, or Epoxide Scaffold

et al. 2016

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“…A very efficient synthesis of (2 S ,3 S ,4 S )- 4 starts from another serine-derived chiron, namely O -benzyl- N -Boc-D-serine [111], which was readily transformed to the Z -olefin 120 containing a benzophenone imine residue as a nitrogen protecting group (Scheme 29). Dihydroxylation of the C=C bond gave a 10:1 mixture with (2 S ,3 S ,4 R )- 121 as a major product which was transformed into the isopropylidene derivative (2 S ,3 S ,4 R )- 122 to facilitate purification.…”

Section: Reviewmentioning

confidence: 99%

“…Dihydroxylation of the C=C bond gave a 10:1 mixture with (2 S ,3 S ,4 R )- 121 as a major product which was transformed into the isopropylidene derivative (2 S ,3 S ,4 R )- 122 to facilitate purification. Hydrogenolysis allowed to remove the N- and O-protecting groups and was followed by the spontaneous cyclization to a pyrrolidine-2-one (3 S ,4 S ,5 R )- 123 [111]. Oxidation of the hydroxymethyl group and acid hydrolysis gave (2 S ,3 S ,4 S )- 4 [112].…”

Section: Reviewmentioning

confidence: 99%

Synthesis of nonracemic hydroxyglutamic acids

Piotrowska¹,

Głowacka²,

Wróblewski³

et al. 2019

Beilstein J. Org. Chem.

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Glutamic acid is involved in several cellular processes though its role as the neurotransmitter is best recognized. For detailed studies of interactions with receptors a number of structural analogues of glutamic acid are required to map their active sides. This review article summarizes syntheses of nonracemic hydroxyglutamic acid analogues equipped with functional groups capable for the formation of additional hydrogen bonds, both as donors and acceptors. The majority of synthetic strategies starts from natural products and relies on application of chirons having the required configuration at the carbon atom bonded to nitrogen (e.g., serine, glutamic and pyroglutamic acids, proline and 4-hydroxyproline). Since various hydroxyglutamic acids were identified as components of complex natural products, syntheses of orthogonally protected derivatives of hydroxyglutamic acids are also covered.

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“…The obtained amino diol was used for the synthesis of protected (2R,3R,4S)-4,7-diamino-2,3-dihydroxyheptanoic acid 76 found in marine natural products, callipeltin A and D [36]. Stereoselective syntheses of D-iminolyxitol 79 [37] and (2S,3S,4S)-3,4-dihydroxyglutamic acid 80 [38] were also successfully achieved by the syn selective dihydroxylation of α,β-unsaturated (Z)-ester from L-serine (Scheme 2).…”

Section: Carbonyl Group-conjugated Allylic Aminesmentioning

confidence: 99%

Stereocontrolled Dihydroxylation Reactions of Acyclic Allylic Amines

Jeon¹,

Shin²,

Kim³

2014

Applied Chemistry for Engineering

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초 록 비고리 알릴아민 화합물의 이중알코올화 반응은 아미노 다이올 구조를 도입할 수 있는 효율적인 합성법으로 아미노 다이올 구조를 포함하는 다양한 생리활성 천연물의 효율적인 합성에 적용될 수 있다. 본 리뷰에서는 기질 그 자체, 혹은 카이랄 리간드를 이용한 다양한 입체선택적 이중알코올화 반응들을 소개하고 이를 실제 천연물의 합성에 적용 한 최근의 반응 결과들을 살펴보고자 한다. AbstractThe dihydroxylation reaction of allylic amines is a facile and useful synthetic method to obtain amino diol structures that are widely found in lots of biologically important natural products. This review will focus on the recent methods of both substrate-controlled and ligand-controlled dihydroxylation reactions of acyclic allylic amines. In addition, several applications of the diastereoselective dihydroxylation methods to asymmetric syntheses of natural products are presented. Figure 1. Dihydroxylation reactions of chiral allylic amines for natural product synthesis. † Corresponding

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syn-Selective dihydroxylation of γ-amino-α,β-unsaturated (Z)-esters from d-serine: stereoselective synthesis of d-iminolyxitol

Cited by 12 publications

References 37 publications

Selective Elaboration of Aminodiols towards Small Ring α‐ and β‐Amino Acid Derivatives that Incorporate an Aziridine, Azetidine, or Epoxide Scaffold

Selective Elaboration of Aminodiols towards Small Ring α‐ and β‐Amino Acid Derivatives that Incorporate an Aziridine, Azetidine, or Epoxide Scaffold

Synthesis of nonracemic hydroxyglutamic acids

Stereocontrolled Dihydroxylation Reactions of Acyclic Allylic Amines

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