Facial Diastereoselectivity in the Paternò–Büchi Reaction of Chiral Silyl Enol Ethers

Thorsten Bach; Kai Jödicke; Kristian Kather; Jürgen Hecht

doi:10.1002/anie.199522711

Facial Diastereoselectivity in the Paternò–Büchi Reaction of Chiral Silyl Enol Ethers

Thorsten Bach, Kai Jödicke, Kristian Kather, Jürgen Hecht

University of Münster

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

30 Scopus citations

Abstract

A single element of chirality determines the configuration of the three newly formed stereogenic centers in the title reaction [Eq. (a)]. In particular, large (R = SiMe₂Ph,tBu) and polar (R = OMe) substituents induce good diastereoselectivities. Simple ring‐opening reactions facilitate a stereoselective approach to acyclic products. (Figure Presented.)

Original language	English
Pages (from-to)	2271-2273
Number of pages	3
Journal	Angewandte Chemie International Edition in English
Volume	34
Issue number	20
DOIs	https://doi.org/10.1002/anie.199522711
State	Published - 3 Nov 1995
Externally published	Yes

Keywords

Paternò–Büchi reactions
asymmetric syntheses
cycloadditions
oxetanes
photochemistry

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10.1002/anie.199522711

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title = "Facial Diastereoselectivity in the Patern{\`o}–B{\"u}chi Reaction of Chiral Silyl Enol Ethers",

abstract = "A single element of chirality determines the configuration of the three newly formed stereogenic centers in the title reaction [Eq. (a)]. In particular, large (R = SiMe2Ph,tBu) and polar (R = OMe) substituents induce good diastereoselectivities. Simple ring‐opening reactions facilitate a stereoselective approach to acyclic products. (Figure Presented.)",

keywords = "Patern{\`o}–B{\"u}chi reactions, asymmetric syntheses, cycloadditions, oxetanes, photochemistry",

author = "Thorsten Bach and Kai J{\"o}dicke and Kristian Kather and J{\"u}rgen Hecht",

year = "1995",

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doi = "10.1002/anie.199522711",

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T1 - Facial Diastereoselectivity in the Paternò–Büchi Reaction of Chiral Silyl Enol Ethers

AU - Bach, Thorsten

AU - Jödicke, Kai

AU - Kather, Kristian

AU - Hecht, Jürgen

PY - 1995/11/3

Y1 - 1995/11/3

N2 - A single element of chirality determines the configuration of the three newly formed stereogenic centers in the title reaction [Eq. (a)]. In particular, large (R = SiMe2Ph,tBu) and polar (R = OMe) substituents induce good diastereoselectivities. Simple ring‐opening reactions facilitate a stereoselective approach to acyclic products. (Figure Presented.)

AB - A single element of chirality determines the configuration of the three newly formed stereogenic centers in the title reaction [Eq. (a)]. In particular, large (R = SiMe2Ph,tBu) and polar (R = OMe) substituents induce good diastereoselectivities. Simple ring‐opening reactions facilitate a stereoselective approach to acyclic products. (Figure Presented.)

KW - Paternò–Büchi reactions

KW - asymmetric syntheses

KW - cycloadditions

KW - oxetanes

KW - photochemistry

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DO - 10.1002/anie.199522711

M3 - Article

AN - SCOPUS:33748731977

SN - 0570-0833

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JO - Angewandte Chemie International Edition in English

JF - Angewandte Chemie International Edition in English

IS - 20

ER -

Facial Diastereoselectivity in the Paternò–Büchi Reaction of Chiral Silyl Enol Ethers

Abstract

Keywords

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