Facial diastereoselectivity in the [2+2]-photocycloaddition of chiral vinylglycine-derived N,N-diallyl amines

Thorsten Bach; Christa Pelkmann; Klaus Harms

doi:10.1016/S0040-4039(99)00158-6

Facial diastereoselectivity in the [2+2]-photocycloaddition of chiral vinylglycine-derived N,N-diallyl amines

Thorsten Bach, Christa Pelkmann, Klaus Harms

Philipps-Universität Marburg

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

21 Scopus citations

Abstract

The vinylglycine-derived N-cinnamyl-N-allyl carbamates 1, 4 and 7 were prepared and their sensitized intramolecular [2+2]-photocycloaddition to the exo-products 2, 5 and 6 was studied (53-77% yield). Perfect facial diastereoselection (d.r. = >95/5) was observed in the photocycloaddition of the rigid oxazolidinone 4 and of the conformationally fixed acyclic carbamate 7.

Original language	English
Pages (from-to)	2103-2104
Number of pages	2
Journal	Tetrahedron Letters
Volume	40
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4039(99)00158-6
State	Published - 12 Mar 1999
Externally published	Yes

Keywords

Amino acids and derivatives
Asymmetric induction
Cycloadditions
Photochemistry

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10.1016/S0040-4039(99)00158-6

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title = "Facial diastereoselectivity in the [2+2]-photocycloaddition of chiral vinylglycine-derived N,N-diallyl amines",

abstract = "The vinylglycine-derived N-cinnamyl-N-allyl carbamates 1, 4 and 7 were prepared and their sensitized intramolecular [2+2]-photocycloaddition to the exo-products 2, 5 and 6 was studied (53-77% yield). Perfect facial diastereoselection (d.r. = >95/5) was observed in the photocycloaddition of the rigid oxazolidinone 4 and of the conformationally fixed acyclic carbamate 7.",

keywords = "Amino acids and derivatives, Asymmetric induction, Cycloadditions, Photochemistry",

author = "Thorsten Bach and Christa Pelkmann and Klaus Harms",

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doi = "10.1016/S0040-4039(99)00158-6",

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T1 - Facial diastereoselectivity in the [2+2]-photocycloaddition of chiral vinylglycine-derived N,N-diallyl amines

AU - Bach, Thorsten

AU - Pelkmann, Christa

AU - Harms, Klaus

PY - 1999/3/12

Y1 - 1999/3/12

N2 - The vinylglycine-derived N-cinnamyl-N-allyl carbamates 1, 4 and 7 were prepared and their sensitized intramolecular [2+2]-photocycloaddition to the exo-products 2, 5 and 6 was studied (53-77% yield). Perfect facial diastereoselection (d.r. = >95/5) was observed in the photocycloaddition of the rigid oxazolidinone 4 and of the conformationally fixed acyclic carbamate 7.

AB - The vinylglycine-derived N-cinnamyl-N-allyl carbamates 1, 4 and 7 were prepared and their sensitized intramolecular [2+2]-photocycloaddition to the exo-products 2, 5 and 6 was studied (53-77% yield). Perfect facial diastereoselection (d.r. = >95/5) was observed in the photocycloaddition of the rigid oxazolidinone 4 and of the conformationally fixed acyclic carbamate 7.

KW - Amino acids and derivatives

KW - Asymmetric induction

KW - Cycloadditions

KW - Photochemistry

UR - http://www.scopus.com/inward/record.url?scp=0033548578&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(99)00158-6

DO - 10.1016/S0040-4039(99)00158-6

M3 - Article

AN - SCOPUS:0033548578

SN - 0040-4039

VL - 40

SP - 2103

EP - 2104

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

Facial diastereoselectivity in the [2+2]-photocycloaddition of chiral vinylglycine-derived N,N-diallyl amines

Abstract

Keywords

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