Novel route to the synthesis of hydroxylated piperidine and pyrrolidine derivatives via the intramolecular reaction of γ-aminoallylstannane with aldehyde

Isao Kadota; Miho Kawada; Shioko Saya; Yoshinori Yamamoto

doi:10.1016/0040-4039(96)00205-5

Novel route to the synthesis of hydroxylated piperidine and pyrrolidine derivatives via the intramolecular reaction of γ-aminoallylstannane with aldehyde

Isao Kadota, Miho Kawada, Shioko Saya, Yoshinori Yamamoto

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

13 Citations (Scopus)

Abstract

The Lewis acid mediated intramolecular reaction of gamma-aminoallyl-stannane 6 gave trans-beta-hydroxypiperidine derivative 7a as a major product. On the other hand, the thermal cyclization of 6 and 8 afforded cis-beta-hydroxypiperidine 7b and pyrrolidine derivative 9b, respectively, with very high stereoselectivity.

Original language	English
Pages (from-to)	2109-2112
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	12
DOIs	https://doi.org/10.1016/0040-4039(96)00205-5
Publication status	Published - Mar 18 1996
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "The Lewis acid mediated intramolecular reaction of gamma-aminoallyl-stannane 6 gave trans-beta-hydroxypiperidine derivative 7a as a major product. On the other hand, the thermal cyclization of 6 and 8 afforded cis-beta-hydroxypiperidine 7b and pyrrolidine derivative 9b, respectively, with very high stereoselectivity.",

author = "Isao Kadota and Miho Kawada and Shioko Saya and Yoshinori Yamamoto",

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AU - Kadota, Isao

AU - Kawada, Miho

AU - Saya, Shioko

AU - Yamamoto, Yoshinori

PY - 1996/3/18

Y1 - 1996/3/18

N2 - The Lewis acid mediated intramolecular reaction of gamma-aminoallyl-stannane 6 gave trans-beta-hydroxypiperidine derivative 7a as a major product. On the other hand, the thermal cyclization of 6 and 8 afforded cis-beta-hydroxypiperidine 7b and pyrrolidine derivative 9b, respectively, with very high stereoselectivity.

AB - The Lewis acid mediated intramolecular reaction of gamma-aminoallyl-stannane 6 gave trans-beta-hydroxypiperidine derivative 7a as a major product. On the other hand, the thermal cyclization of 6 and 8 afforded cis-beta-hydroxypiperidine 7b and pyrrolidine derivative 9b, respectively, with very high stereoselectivity.

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M3 - Article

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JF - Tetrahedron Letters

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ER -

Novel route to the synthesis of hydroxylated piperidine and pyrrolidine derivatives via the intramolecular reaction of γ-aminoallylstannane with aldehyde

Abstract

ASJC Scopus subject areas

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