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Oxidative aminomercuration of 2‐propyn‐1‐ols. Stereoselective syntheses and structures of cis ‐[1,4]oxazino[3,2‐ b ]‐1,4‐oxazine derivatives
Author(s) -
Barluenga José,
Aznar Fernando,
Liz Ramón,
Cabal MaríaPaz,
Cano Félix H.,
FocesFoces Concepción
Publication year - 1986
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19861190313
Subject(s) - chemistry , stereoselectivity , oxidative phosphorylation , stereochemistry , chloride , mercury (programming language) , anomer , medicinal chemistry , organic chemistry , catalysis , biochemistry , computer science , programming language
The reactions of 2‐Propin‐1‐ols 1 with 2‐amino alcohols 7 and mercury(II) chloride start with an oxidative aminomercuration step followed by a series of highly stereoselective processes leading to cis ‐[1,4]oxazino[3,2‐ b ]‐1,4‐oxazine derivatives 10 . X ‐Ray analyses of 10c,f,g show that these compounds have the same geometrical arrangement around their central fusion bond in such a way that anomeric stabilisation reaches a maximum.