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  • Gold and BINOL-phosphoric acid catalyzed enantioselective hydroamination/N-sulfonyliminium cyclization cascade.

Gold and BINOL-phosphoric acid catalyzed enantioselective hydroamination/N-sulfonyliminium cyclization cascade.

Organic letters (2013-08-30)
Alex W Gregory, Pavol Jakubec, Paul Turner, Darren J Dixon
PMID23985045
ABSTRACT

A highly enantioselective hydroamination/N-sulfonyliminium cyclization cascade is reported using a combination of gold(I) and chiral phosphoric acid catalysts. An initial 5-exo-dig hydroamination and a subsequent phosphoric acid catalyzed cyclization process provide access to complex sulfonamide scaffolds in excellent yield and high enantiocontrol. The method can be extended to lactam derivatives, with excellent yields and enantiomeric excesses of up to 93% ee.

MATERIALS
Product Number
Brand
Product Description
698822
Sigma-Aldrich
Phosphoric acid solution, NMR reference standard, 85% in D2O (99.9 atom % D), NMR tube size 5 mm × 8 in.
699608
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345245
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Phosphoric acid, 85 wt. % in H2O, 99.99% trace metals basis
79617
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04102
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452289
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79622
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Phosphoric acid, puriss. p.a., crystallized, ≥99.0% (T)
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438081
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695017
Sigma-Aldrich
Phosphoric acid, ACS reagent, ≥85 wt. % in H2O
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Sigma-Aldrich
Phosphoric acid, puriss., meets analytical specification of Ph. Eur., BP, NF, FCC, 85.0-88.0%