Journal
ORGANIC LETTERS
Volume 21, Issue 2, Pages 519-523Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03833
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- Deutsche Forschungsgemeinschaft [SCHN 441/11-2]
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We describe herein an organocatalytic, diastereo- and enantioselective [6 + 2]-cycloaddition toward the synthesis of densely substituted 2,3-dihydro-1H-pyrrolizines bearing three contiguous stereogenic centers which are obtained with good yields, as single diastereomers, and with excellent enantioselectivity. A crucial feature of this one-step process leading to a prominent structural motif in many biologically active natural products is a BINOL-derived phosphoric acid catalyzed reaction of 1H-pyrrole-2-yl carbinols with 2-vinylindoles via the corresponding hydrogen-bonded chiral 2-methide-2H-pyrroles.
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