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Asymmetric Elimination with High Induction: Synthesis of 1‐Alkenylsulfoximides with Axial and Central Chirality
Author(s) -
Erdelmeier Irene,
Gais HansJoachim,
Lindner Hans J.
Publication year - 1986
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.198609351
Subject(s) - yield (engineering) , chirality (physics) , asymmetric induction , ketone , chemistry , elimination reaction , stereochemistry , combinatorial chemistry , medicinal chemistry , enantioselective synthesis , catalysis , organic chemistry , physics , nambu–jona lasinio model , quark , chiral symmetry breaking , thermodynamics , quantum mechanics
The elimination of LiOSiMe 3 in the title reaction (1 → 2) is accomplished in 91% yield and with ≥ 98% diastereoselectivity by reaction of 1 with n BuLi. Compound 1 is prepared by reaction of the corresponding ketone with LiCH 2 S(O)(NMe)Ph. The elimination can be used, in the sense of an inverse Peterson reaction, for asymmetric carbonylolefination.