Affiliation:
1. Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA.
Abstract
Lewis acid catalysis tackled by tag team
Molecular catalysts with two closely spaced nitrogen-hydrogen groups can act like a tweezer, activating a carbon center by latching onto a leaving group through double hydrogen bonding and then pulling it away. In the resultant ion pair, the shape of the catalyst can bias an ensuing reaction to favor just one of two possible mirror-image products. Banik
et al.
used this motif to activate a Lewis acid cocatalyst, pulling a leaving group off silicon instead of carbon (see the Perspective by Mattson). The combined pair of catalysts is more effective for reactions such as asymmetric cycloadditions that involve weaker leaving groups on carbon.
Science
, this issue p.
761
; see also p.
720
Funder
National Institutes of Health
Publisher
American Association for the Advancement of Science (AAAS)
Cited by
160 articles.
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