Palladium(II)-Catalyzed Oxidative Cyclization of Allylic Tosylcarbamates: Scope, Derivatization, and Mechanistic Aspects

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Palladium(II)-Catalyzed Oxidative Cyclization of Allylic Tosylcarbamates: Scope, Derivatization, and Mechanistic Aspects. / Joosten, Antoine; Persson, Andreas K. A.; Millet, Renaud; Johnson, Magnus; Backvall, Jan-E.

I: Chemistry: A European Journal, Vol. 18, Nr. 47, 2012, s. 15151-15157.

Forskningsoutput: TidskriftsbidragÖversiktsartikel

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Joosten, Antoine ; Persson, Andreas K. A. ; Millet, Renaud ; Johnson, Magnus ; Backvall, Jan-E. / Palladium(II)-Catalyzed Oxidative Cyclization of Allylic Tosylcarbamates: Scope, Derivatization, and Mechanistic Aspects. I: Chemistry: A European Journal. 2012 ; Vol. 18, Nr. 47. s. 15151-15157.

RIS

TY - JOUR

T1 - Palladium(II)-Catalyzed Oxidative Cyclization of Allylic Tosylcarbamates: Scope, Derivatization, and Mechanistic Aspects

AU - Joosten, Antoine

AU - Persson, Andreas K. A.

AU - Millet, Renaud

AU - Johnson, Magnus

AU - Backvall, Jan-E.

PY - 2012

Y1 - 2012

N2 - A highly selective oxidative palladium(II)-catalyzed (Wacker-type) cyclization of readily available allylic tosylcarbamates is reported. This operationally simple catalytic reaction furnishes tosyl-protected vinyl-oxazolidinones, common precursors to syn-1,2-amino alcohols, in high yield and excellent diasteroselectivity (>20:1). It is demonstrated that both stoichiometric amounts of benzoquinone (BQ) as well as aerobic reoxidation (molecular oxygen) is suitable for this transformation. The title reaction is shown to proceed through overall trans-amidopalladation of the olefin followed by beta-hydride elimination. This process is scalable and the products are suitable for a range of subsequent transformations such as: kinetic resolution (KR) and oxidative Heck-, Wacker-, and metathesis reactions.

AB - A highly selective oxidative palladium(II)-catalyzed (Wacker-type) cyclization of readily available allylic tosylcarbamates is reported. This operationally simple catalytic reaction furnishes tosyl-protected vinyl-oxazolidinones, common precursors to syn-1,2-amino alcohols, in high yield and excellent diasteroselectivity (>20:1). It is demonstrated that both stoichiometric amounts of benzoquinone (BQ) as well as aerobic reoxidation (molecular oxygen) is suitable for this transformation. The title reaction is shown to proceed through overall trans-amidopalladation of the olefin followed by beta-hydride elimination. This process is scalable and the products are suitable for a range of subsequent transformations such as: kinetic resolution (KR) and oxidative Heck-, Wacker-, and metathesis reactions.

KW - amidopalladation

KW - cyclization

KW - oxazolidinones

KW - oxidation

KW - palladium

U2 - 10.1002/chem.201202359

DO - 10.1002/chem.201202359

M3 - Review article

C2 - 23033176

VL - 18

SP - 15151

EP - 15157

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

SN - 1521-3765

IS - 47

ER -