Carbohydrate-Derived Chiral Furanosidic α,β-Unsaturated Aldehydes in Conjugate and Diels-Alder Addition Reactions. Steric Hindrance by the Anomeric Substituent

DOI: 10.1021/jo00307a018

Source and publish data:

Journal of Organic Chemistry p. 5477 - 5483 (1990)

Update date:2022-08-02

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Authors:

Rehnberg, Nicola

Sundin, Anders

Magnusson, Goeran

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Article abstract of DOI:10.1021/jo00307a018

The title aldehydes (1r, 1s, 2, and 3) underwent virtually diastereospecific conjugate addition by lithium methylcyanocuprate.The bulkiness of the anomeric benzyloxy or methoxy groups direct the attacking nucleophile to the less hindered side of the furan

Full text of DOI:10.1021/jo00307a018

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