Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom