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Highly Selective Addition of a Broad Spectrum of Trimethylsilane Pro‐nucleophiles to N ‐ tert ‐Butanesulfinyl Imines
Author(s) -
Das Manas,
O'Shea Donal F.
Publication year - 2015
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.201503354
Subject(s) - electrophile , chemistry , nucleophile , broad spectrum , reagent , enantioselective synthesis , lewis acids and bases , combinatorial chemistry , organic chemistry , catalysis
Addition of organotrimethylsilane reagents to chiral N ‐ tert ‐butanesulfinyl imines can be achieved in good yields and with excellent diastereoselectivities by employing TMSO − /Bu 4 N + as a Lewis base activator in THF. A variety of aliphatic, aromatic, heteroaromatic and organometallic chiral imines were utilised as electrophiles for the synthesis of enantioenriched N ‐ tert ‐butanesulfinyl amides. Remarkably, the same sets of reaction conditions could be used with a highly diverse range of bench‐stable organotrimethylsilane reagents, which highlights the generality and robustness of this methodology.