Syntheses of iminolyxitols via tandem reduction-alkenylation of O'Donnell's Schiff bases

Hossein Razavi; Robin Polt

doi:10.1016/S0040-4039(98)00495-X

Syntheses of iminolyxitols via tandem reduction-alkenylation of O'Donnell's Schiff bases

Hossein Razavi, Robin Polt

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

The concise enantioselective synthesis of iminolyxitol glycosidase inhibitors starting from benzophenone imines of D-serine and L-alanine esters is very efficient. The reductive-alkenylation of the Schiff bases followed by substrate-directed dihydroxylation and amino dehydration gave the polyhydroxylated pyrrolidines in excellent overall yields (19.6% for 3 → 8. 9.9% for 2 → 13.).

Original language	English (US)
Pages (from-to)	3371-3374
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4039(98)00495-X
State	Published - May 21 1998

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "The concise enantioselective synthesis of iminolyxitol glycosidase inhibitors starting from benzophenone imines of D-serine and L-alanine esters is very efficient. The reductive-alkenylation of the Schiff bases followed by substrate-directed dihydroxylation and amino dehydration gave the polyhydroxylated pyrrolidines in excellent overall yields (19.6% for 3 → 8. 9.9% for 2 → 13.).",

author = "Hossein Razavi and Robin Polt",

note = "Funding Information: Acknowledgements. We are grateful to the NSF for support (CHE-9526909). H.R. would like to thank the",

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AU - Razavi, Hossein

AU - Polt, Robin

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PY - 1998/5/21

Y1 - 1998/5/21

N2 - The concise enantioselective synthesis of iminolyxitol glycosidase inhibitors starting from benzophenone imines of D-serine and L-alanine esters is very efficient. The reductive-alkenylation of the Schiff bases followed by substrate-directed dihydroxylation and amino dehydration gave the polyhydroxylated pyrrolidines in excellent overall yields (19.6% for 3 → 8. 9.9% for 2 → 13.).

AB - The concise enantioselective synthesis of iminolyxitol glycosidase inhibitors starting from benzophenone imines of D-serine and L-alanine esters is very efficient. The reductive-alkenylation of the Schiff bases followed by substrate-directed dihydroxylation and amino dehydration gave the polyhydroxylated pyrrolidines in excellent overall yields (19.6% for 3 → 8. 9.9% for 2 → 13.).

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Syntheses of iminolyxitols via tandem reduction-alkenylation of O'Donnell's Schiff bases

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