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  • Síntesis Asimétrica E

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    This document discusses different types of selectivity in organic synthesis, including chemoselectivity, regioselectivity, and enantioselectivity. Chemoselectivity refers to the relative reactivity of different functional groups in a molecule. Regioselectivity is the selectivity between different aspects of the same functional group. Enantioselectivity deals with asymmetric synthesis and producing chiral molecules like amino acids and DNA carbohydrates. The document also mentions the formation of enolates, noting that ketones typically form Z enolates while esters form E enolates, and that adding HMPA can reverse the stereoselectivity of deprotonation.

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    10. Síntesis Asimétrica E (1)

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    This document discusses different types of selectivity in organic synthesis, including chemoselectivity, regioselectivity, and enantioselectivity. Chemoselectivity refers to the relative reactivity of different functional groups in a molecule. Regioselectivity is the selectivity between different aspects of the same functional group. Enantioselectivity deals with asymmetric synthesis and producing chiral molecules like amino acids and DNA carbohydrates. The document also mentions the formation of enolates, noting that ketones typically form Z enolates while esters form E enolates, and that adding HMPA can reverse the stereoselectivity of deprotonation.

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    © All Rights Reserved
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    11 views57 pages

    Síntesis Asimétrica E

    Uploaded by

    BrueliPalacin
    This document discusses different types of selectivity in organic synthesis, including chemoselectivity, regioselectivity, and enantioselectivity. Chemoselectivity refers to the relative reactivity of different functional groups in a molecule. Regioselectivity is the selectivity between different aspects of the same functional group. Enantioselectivity deals with asymmetric synthesis and producing chiral molecules like amino acids and DNA carbohydrates. The document also mentions the formation of enolates, noting that ketones typically form Z enolates while esters form E enolates, and that adding HMPA can reverse the stereoselectivity of deprotonation.

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    of 57

    Sntesis orgnica

    Mestranol

    Muscona

    Situaciones para analizar en sntesis orgnica

    Tipos de selectividad: Depende de la presencia de los grupos funcionales presentes

    The chemoselectivity
    It is matter of reactivity .

    The chemoselectivity
    Which is more reactive ??

    Otros grupos funcionales con carbonilos?

    The chemoselectivity

    The chemoselectivity
    Reduccin de grupos carbonilos con agentes reductores

    The chemoselectivity

    Y con LiAlH4?

    Chemoselectivity

    Selectivity between two functional groups

    CHEMOSELECTIVITY: when we want that one and not another functional


    group in a molecule reacts

    relative reactivity of two different functional groups


    HO

    HO

    Ac2O
    NH2

    N
    H

    reaction of one of two identical functional groups


    HO

    base
    OH

    MeO

    MeI

    OH

    reaction of a group once when it may react again


    S2-

    R S-

    R S R

    Regioselectivity

    Selectivity between different aspects of the same functional group

    Enantioselectivity

    Sntesis asimtrica

    Otros: aminocidos tienen configuracin L; carbohidratos del ADN son quirales

    R-Sulcatol

    S-Sulcatol

    Mecanismo??

    Formacin de enolatos

    Formacin de enolatos con steres


    The stereoselective formation of enolates has been rationalized with the Ireland model

    Formacin de enolatos

    For ketones, most enolization conditions give Z enolates. For esters, most enolization
    conditions give E enolates.

    The addition of HMPA is known to reverse the stereoselectivity of deprotonation.

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