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1 article(s) from Schefzig, Luise

Iodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions

Michal Medvecký,
Igor Linder,
Luise Schefzig,
Hans-Ulrich Reissig and
Reinhold Zimmer

Beilstein J. Org. Chem. 2016, 12, 2898–2905, doi:10.3762/bjoc.12.289

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Scheme 1: Access to enantiopure 3,6-dihydro-1,2-oxazines 3 via lithiated alkoxyallenes 1 and carbohydrate-der...

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Scheme 2: Iodination of 1,2-oxazines syn-3a–c and anti-3a,d leading to 5-iodo-substituted 1,2-oxazines syn-4a...

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Scheme 3: Sonogashira reactions of 4-methoxy-1,2-oxazines syn-4a, anti-4a and anti-4d leading to 5-alkynyl-su...

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Scheme 4: Sonogashira reactions of D-glyceraldehyde-derived 1,2-oxazines syn-4a–c leading to 5-alkynyl-substi...

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Scheme 5: Heck reactions of 1,2-oxazine syn-4a leading to 5-alkenyl-substituted 1,2-oxazines syn-13, syn-14 a...

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Scheme 6: Suzuki–Miyaura reactions of 1,2-oxazines syn-4a, syn-4b and anti-4d leading to 5-styryl-substituted...

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Scheme 7: Cross-coupling reaction of 1,2-oxazine anti-4d leading to 5-cyano-substituted 1,2-oxazine anti-25.

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Scheme 8: Desilylation of 1,2-oxazine syn-5 and subsequent click reaction with benzyl azide leading to 5-(1,2...

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Scheme 9: Hydrogenation of 1,2-oxazine syn-21 leading to γ-amino alcohols 27a,b and subsequent ring closure t...

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Scheme 10: Hydrogenation of 1,2-oxazine anti-24 to products anti-29 and anti-30.

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Published 29 Dec 2016

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