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Reductive Samariation of Anomeric 2‐Pyridyl Sulfones with Catalytic Nickel: An Unexpected Improvement in the Synthesis of 1,2‐ trans ‐Diequatorial C‐Glycosyl Compounds
Author(s) -
Miquel Nicolas,
Doisneau Gilles,
Beau JeanMarie
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20001117)39:22<4111::aid-anie4111>3.0.co;2-c
Subject(s) - glycosyl , anomer , catalysis , chemistry , nickel , combinatorial chemistry , organic chemistry
How can the competing β ‐elimination of leaving groups from anomeric organometallic reagents derived from neutral hexopyranoses be minimized? Answer: Catalytic amounts of nickel( II ) iodide added to the reductive samariation of anomeric 2‐pyridyl sulfones will suffice. The overall result is a fast, efficient, and highly stereoselective synthesis of C‐glycosyl compounds, such as 3 , from sulfone 1 (2‐Py=2‐pyridyl) and aldehyde 2 .