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Iron‐Promoted, Regio‐ and Stereoselective Allylic Substitutions for the Synthesis of Alkenyl Sulfones Substituted at C‐3
Author(s) -
Enders Dieter,
Jandeleit Bernd,
Raabe Gerhard
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199419491
Subject(s) - stereoselectivity , nucleophile , allylic rearrangement , chirality (physics) , chemistry , tetrafluoroborate , enantiomer , regioselectivity , medicinal chemistry , stereochemistry , sulfone , organic chemistry , catalysis , ionic liquid , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
Almost complete transfer of chirality is observed in the nucleophilic addition of various carbon and nitrogen nucleophiles (Nu) to the highly enantiomerically enriched 1‐phenylsulfonyl‐substituted (η 3 ‐allyl)tetracarbonyliron(1+) tetrafluoroborate with planar chirality ( 1 ; de, ee > 98%). Oxidative decomplexation yields alkenyl phenyl sulfones 2 with a range of subtituents at C‐3 and high enantiomeric purity ( ee ≥ 96%).