Furyl- and Tetrahydrofuryl-alkylamines

McCarthy, Walter C.; Kahl, Raymond J.

doi:10.1021/jo01116a016

J. Org. Chem.

1956

DOI: 10.1021/jo01116a016

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Furyl- and Tetrahydrofuryl-alkylamines

Walter C. McCarthy¹,

Raymond J. Kahl²

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Cited by 9 publications

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Diastereo- and Enantioselective Synthesis of Vicinal Amino Alcohols by Oxa Michael Addition ofN-Formylnorephedrine to Nitro Alkenes

Enders¹,

Haertwig²,

Raabe³

et al. 1998

Eur. J. Org. Chem.

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The first intermolecular asymmetric oxa Michael additions with removable chirality information within the hydroxide source are reported. As enantiopure oxygen nucleophile functioning as chiral hydroxide equivalent N‐formylnorephedrine (7) was used and conjugate additions to aliphatic (E)‐nitro alkenes 2a–j were carried out in good yields (35‐87%) and excellent diastereomeric excesses (de = 94–≥98%). After reduction of the nitro group and protection of the amino function (11a–h, 73‐87%, both steps), the cleavage of the auxiliary occurred without epimerisation (69‐99%) using Na/NH3. The Boc‐protected 2‐amino alcohols 12a–h could be obtained in good overall yields (30‐58 %, four steps) and excellent diastereomeric and enantiomeric excesses (de, ee = 94–≥98%). Transition states explaining the overall stereochemical outcome are presented based on the absolute configuration determined by X‐ray structure analysis on 8b.

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Diastereo- and Enantioselective Synthesis of Vicinal Amino Alcohols by Oxa Michael Addition ofN-Formylnorephedrine to Nitro Alkenes

Enders¹,

Haertwig²,

Raabe³

et al. 1998

Eur. J. Org. Chem.

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Highly Flexible Synthesis of 2-Arylethylamine Derivatives

Siebeneicher

Doye

2002

Eur. J. Org. Chem.

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A new and highly flexible procedure for the synthesis of 2-arylethylamine derivatives is described. By the new procedure, the target compounds can be synthesized with high diversity in three steps from aryl halides, terminal alkynes, and primary amines. The reaction sequence starts with a palladium-catalyzed coupling of an aryl halide and a terminal alkyne (Sonogashira coupling). A subsequent Cp 2 TiMe 2 -cata-

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N‐Heteroaralkyl substituted α‐amidinium thiolsulfates

Parulkar

Bauer

1966

Journal of Heterocyclic Chem

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Furyl- and Tetrahydrofuryl-alkylamines

Cited by 9 publications

References 0 publications

Diastereo- and Enantioselective Synthesis of Vicinal Amino Alcohols by Oxa Michael Addition ofN-Formylnorephedrine to Nitro Alkenes

Diastereo- and Enantioselective Synthesis of Vicinal Amino Alcohols by Oxa Michael Addition ofN-Formylnorephedrine to Nitro Alkenes

Highly Flexible Synthesis of 2-Arylethylamine Derivatives

N‐Heteroaralkyl substituted α‐amidinium thiolsulfates

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