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Synthesis of 1,2‐Amino Alcohols by Sigmatropic Rearrangements of 3‐( N ‐Tosylamino)allylic Alcohol Derivatives
Author(s) -
Barbazanges Marion,
Meyer Christophe,
Cossy Janine,
Turner Peter
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201003265
Subject(s) - sigmatropic reaction , allylic rearrangement , chemistry , stereoselectivity , chirality (physics) , nitrogen atom , alcohol , stereochemistry , organic chemistry , ring (chemistry) , catalysis , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Sigmatropic rearrangements of 3‐( N ‐tosylamino)allylic alcohol derivatives, a particular subclass of functionalized enamides, have been investigated. Whereas the presence of the nitrogen atom alters the stereochemical outcome of Ireland–Claisen rearrangements of glycolates derived from such substrates, [2,3]‐Wittig rearrangements of α‐allyloxy acetamides or propargylic ethers derivatives provide access to a wide variety of functionalized 1,2‐amino alcohols usually with high levels of stereocontrol, as well as to heterocyclic compounds. The stereoselectivity issues of these rearrangements (1,2‐diastereoselectivity, auxiliary‐induced diastereoselection, chirality transfer, and double stereodifferentiation) were thoroughly investigated.