Asymmetric synthesis of β-alkoxycyclic ethers via the intramolecular cyclization of group 14 allyls containing chiral acetals

Isao Kadota; Koichi Miura; Yoshinori Yamamoto

doi:10.1039/C39940001953

Asymmetric synthesis of β-alkoxycyclic ethers via the intramolecular cyclization of group 14 allyls containing chiral acetals

Isao Kadota, Koichi Miura, Yoshinori Yamamoto

Research output: Contribution to journal › Article

20 Citations (Scopus)

Abstract

Treatment of an allylic tin-bearing chiral acetal 1a with TiCl ₄-PPh₃ gives the (2S, 3R) isomer 2 with high diastereoselectivity (2 : 3 = 93 : 7), whereas the reaction of an allylic silane derivative 1f affords predominantly the (2R, 3S) isomer 3 (2 : 3 = 37 : 63).

Original language	English
Pages (from-to)	1953-1954
Number of pages	2
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	17
DOIs	https://doi.org/10.1039/C39940001953
Publication status	Published - Dec 1 1994
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine

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title = "Asymmetric synthesis of β-alkoxycyclic ethers via the intramolecular cyclization of group 14 allyls containing chiral acetals",

abstract = "Treatment of an allylic tin-bearing chiral acetal 1a with TiCl 4-PPh3 gives the (2S, 3R) isomer 2 with high diastereoselectivity (2 : 3 = 93 : 7), whereas the reaction of an allylic silane derivative 1f affords predominantly the (2R, 3S) isomer 3 (2 : 3 = 37 : 63).",

author = "Isao Kadota and Koichi Miura and Yoshinori Yamamoto",

year = "1994",

month = dec,

day = "1",

doi = "10.1039/C39940001953",

language = "English",

pages = "1953--1954",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

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T1 - Asymmetric synthesis of β-alkoxycyclic ethers via the intramolecular cyclization of group 14 allyls containing chiral acetals

AU - Kadota, Isao

AU - Miura, Koichi

AU - Yamamoto, Yoshinori

PY - 1994/12/1

Y1 - 1994/12/1

N2 - Treatment of an allylic tin-bearing chiral acetal 1a with TiCl 4-PPh3 gives the (2S, 3R) isomer 2 with high diastereoselectivity (2 : 3 = 93 : 7), whereas the reaction of an allylic silane derivative 1f affords predominantly the (2R, 3S) isomer 3 (2 : 3 = 37 : 63).

AB - Treatment of an allylic tin-bearing chiral acetal 1a with TiCl 4-PPh3 gives the (2S, 3R) isomer 2 with high diastereoselectivity (2 : 3 = 93 : 7), whereas the reaction of an allylic silane derivative 1f affords predominantly the (2R, 3S) isomer 3 (2 : 3 = 37 : 63).

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M3 - Article

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SP - 1953

EP - 1954

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

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ER -