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Stereoselective Synthesis of Alcohols, XLIX. Tetrahydro‐4‐pyranols and 4‐Piperidinols by Intramolecular Allylboration Reaction
Author(s) -
Hoffmann Reinhard W.,
Hense Achim
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960807
Subject(s) - intramolecular force , chemistry , stereospecificity , stereoselectivity , medicinal chemistry , stereochemistry , organic chemistry , catalysis
trans ‐ and cis ‐3‐Vinyltetrahydropyran‐4‐ol ( 11 ) and ( 12 ) as well as derivatives of trans ‐ and cis ‐3‐vinyl‐4‐piperidinol ( 25 ) and ( 33 ) were synthesized by essentially stereospecific intramolecular allylboration reactions: The ( Z )‐allylboronates 15 and 32 were converted into the cis ‐disubstituted heterocycles the ( E )‐allylboronates 9 and 23 into the trans ‐disubstituted heterocycles.