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Highly Diastereo‐ and Enantioselective Synthesis of Protected anti ‐1,3‐Diols
Author(s) -
Enders Dieter,
Hundertmark Thomas,
Lampe Cornelia,
Jegelka Udo,
Scharfbillig Ilse
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199812)1998:12<2839::aid-ejoc2839>3.0.co;2-7
Subject(s) - enantioselective synthesis , deoxygenation , chemistry , hydrazone , acetonide , total synthesis , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , medicine , surgery , triamcinolone acetonide
An efficient asymmetric synthesis of protected anti ‐1,3‐diols 5 ( de ≥ 98%, ee = 92‐98%) from 2,2‐dimethyl‐1,3‐dioxan‐5‐one SAMP hydrazone 1 is described. The key steps are the diastereo‐ and enantioselective α,α′‐bisalkylation followed by reduction of the ketones 2 and a variant of the Barton–McCombie deoxygenation. The new method allows the synthesis of acetonide‐protected anti ‐1,3‐diols with a broad range of substituents in good overall yields (31‐69%).