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 journalArticle

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 languageEnglish
Pages (from-to)1953-1954
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number17
DOIs
Publication statusPublished - 1994
Externally publishedYes

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Silanes
Acetals
Ethers
Tin
Cyclization
Isomers
Bearings (structural)
Derivatives

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

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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",
doi = "10.1039/C39940001953",
language = "English",
pages = "1953--1954",
journal = "Chemical Communications",
issn = "1359-7345",
publisher = "Royal Society of Chemistry",
number = "17",

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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

Y1 - 1994

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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DO - 10.1039/C39940001953

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JO - Chemical Communications

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