Asymmetric syntheses with amino acids

Martens, Jürgen

doi:10.1007/3-540-13569-3_5

Cited by 78 publications

(3 citation statements)

References 446 publications

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“…Proline-catalyzed enantioselective aldol reactions were first reported in the 1970s in the context of the Hajos−Parrish−Eder−Sauer−Wiechert reaction (i.e., 1 → 2 ; Scheme ) .…”

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confidence: 99%

Enantioselective Direct Intermolecular Aldol Reactions with Enantiotopic Group Selectivity and Dynamic Kinetic Resolution

2005

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[reaction: see text] Proline-catalyzed aldol reactions of tetrahydro-4H-thipyranone with racemic 1,4-dioxa-8-thia-spiro[4.5]decane-6-carboxaldehyde and with meso/dl 1,4-dioxa-8-thiaspiro[4.5]decane-6,10-dicarboxaldehyde proceed with dynamic kinetic resolution and give single adducts in good yields with excellent ee's. The high enantiotopic group selectivity results from the high intrinsic diastereoface selectivity of the aldehydes. These reactions significantly extend the scope of the enantioselective direct aldol reaction and constitute simple and efficient syntheses of useful tetrapropionate synthons.

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“…Proline-catalyzed enantioselective aldol reactions were first reported in the 1970s in the context of the Hajos−Parrish−Eder−Sauer−Wiechert reaction (i.e., 1 → 2 ; Scheme ) .…”

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confidence: 99%

Enantioselective Direct Intermolecular Aldol Reactions with Enantiotopic Group Selectivity and Dynamic Kinetic Resolution

2005

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“…The chiral pool of natural L-a-amino acids provides a convenient source of optically active compounds that have been utilized by organic chemists for various purposes (Martens 1984;Coppola & Schuster 1987). One possibility is to convert them into the corresponding Nprotected a-amino aldehydes, because these are potentially useful building blocks in such C-C bond-forming reactions as Grignard and aldol additions.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective reactions of chiral α-amino aldehydes

1988

Phil. Trans. R. Soc. Lond. A

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Optically active α-amino acids can be converted into the corresponding doubly protected N,N-dibenzyl α-amino aldehydes. These react diastereoselectively with Grignard reagents, lithium enolates and Me 3 SiCN/ZnX 2 to provide the nonchelation-controlled adducts. Molecular modelling explains some of the results. The sense of stereoselectivity can be reversed if Lewis acidic chelating reagents are used. Undesired racemization does not occur.

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“…13 To the best of our knowledge, the synthesis of an (R)-Garner-type aldehyde starting from L-serine is unprecedented, and it constitutes an attractive source of chiral nonracemic starting material for many asymmetric syntheses. 14 In this paper, we describe a new method for the synthesis of the (R)-Garner-type aldehyde 13, and for the subsequent addition of a vinyl organocerium compound to provide intermediate syn-14 for (+)-furanomycin synthesis.…”

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confidence: 99%

Synthesis of an (R)-Garner-type Aldehyde from l-Serine: Useful Building Block for a (+)-Furanomycin Derivative

Bartoli¹,

Antonio²,

Fiocchi³

et al. 2009

Synthesis

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+)-Furanomycin is an antibiotic that substitutes for Lisoleucine in bacterial protein translation. We propose here a new short synthesis of a useful intermediate, a 1,2-diprotected 2-aminopent-4-ene-1,3-diol, starting from the inexpensive natural amino acid L-serine, and via a Garner-type aldehyde. The (R)-a-amino aldehyde was obtained by the construction of an oxazoline ring between the N-protected amino group and the hydroxy group that resulted from reduction of the carboxylic acid functionality of Lserine.

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Asymmetric syntheses with amino acids

Cited by 78 publications

References 446 publications

Enantioselective Direct Intermolecular Aldol Reactions with Enantiotopic Group Selectivity and Dynamic Kinetic Resolution

Enantioselective Direct Intermolecular Aldol Reactions with Enantiotopic Group Selectivity and Dynamic Kinetic Resolution

Stereoselective reactions of chiral α-amino aldehydes

Synthesis of an (R)-Garner-type Aldehyde from l-Serine: Useful Building Block for a (+)-Furanomycin Derivative

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