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Merck

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
RESUMEN

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.

MATERIALES
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695017
Sigma-Aldrich
Ácido fosfórico, ACS reagent, ≥85 wt. % in H2O
345245
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Ácido fosfórico, 85 wt. % in H2O, 99.99% trace metals basis
438081
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Ácido fosfórico, ACS reagent, ≥85 wt. % in H2O
30417
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Ácido fosfórico, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥85%
466123
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Ácido fosfórico, crystalline, ≥99.999% trace metals basis
79622
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Ácido fosfórico, puriss. p.a., crystallized, ≥99.0% (T)
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Ácido fosfórico, puriss., meets analytical specification of Ph. Eur., BP, NF, FCC, 85.0-88.0%
79617
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Ácido fosfórico, BioUltra, ≥85% (T)
452289
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Ácido fosfórico, ≥85 wt. % in H2O, ≥99.999% trace metals basis
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Ácido fosfórico, BioReagent, suitable for insect cell culture, 85%
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