Alternate mode of palladium-catalyzed alkynyliminium ion cyclizations affording stereodefined N-alkyl-3-alkylidenepyrrolidines

Hirokazu Tsukamoto; Mitsugu Shiraishi; Takayuki Doi

doi:10.1021/ol402685g

Alternate mode of palladium-catalyzed alkynyliminium ion cyclizations affording stereodefined N-alkyl-3-alkylidenepyrrolidines

Hirokazu Tsukamoto, Mitsugu Shiraishi, Takayuki Doi

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

Pd/P(c-C₆H₁₁)₃-catalyzed alkynyliminium ion cyclization in the presence of organoboronic acids affords stereodefined N-alkyl-3-alkylidenepyrrolidines. The distinctive cis-selective addition of the boronic acids and the iminium ions across the alkyne would result from favored 5-exo- or 6-exo-dig cyclization through oxidative addition of the formaldiminium ions to Pd(0).

Original language	English
Pages (from-to)	5932-5935
Number of pages	4
Journal	Organic letters
Volume	15
Issue number	23
DOIs	https://doi.org/10.1021/ol402685g
Publication status	Published - 2013 Dec 6

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol402685g

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abstract = "Pd/P(c-C6H11)3-catalyzed alkynyliminium ion cyclization in the presence of organoboronic acids affords stereodefined N-alkyl-3-alkylidenepyrrolidines. The distinctive cis-selective addition of the boronic acids and the iminium ions across the alkyne would result from favored 5-exo- or 6-exo-dig cyclization through oxidative addition of the formaldiminium ions to Pd(0).",

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AU - Tsukamoto, Hirokazu

AU - Shiraishi, Mitsugu

AU - Doi, Takayuki

PY - 2013/12/6

Y1 - 2013/12/6

N2 - Pd/P(c-C6H11)3-catalyzed alkynyliminium ion cyclization in the presence of organoboronic acids affords stereodefined N-alkyl-3-alkylidenepyrrolidines. The distinctive cis-selective addition of the boronic acids and the iminium ions across the alkyne would result from favored 5-exo- or 6-exo-dig cyclization through oxidative addition of the formaldiminium ions to Pd(0).

AB - Pd/P(c-C6H11)3-catalyzed alkynyliminium ion cyclization in the presence of organoboronic acids affords stereodefined N-alkyl-3-alkylidenepyrrolidines. The distinctive cis-selective addition of the boronic acids and the iminium ions across the alkyne would result from favored 5-exo- or 6-exo-dig cyclization through oxidative addition of the formaldiminium ions to Pd(0).

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Alternate mode of palladium-catalyzed alkynyliminium ion cyclizations affording stereodefined N-alkyl-3-alkylidenepyrrolidines

Abstract

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