New chiral auxiliaries and new optically pure ketene equivalents derived from tartaric acids. Improved synthesis of (−)-7-oxabicyclo[2.2.1]hept-5-en-2-one.
1
Section de Chimie de l'Université, 2 Rue de la Barre, CH-1005 Lausanne Switzerland
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Publication type: Journal Article
Publication date: 1990-01-01
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
Condensation of di-O-acetyl( R,R )- and ( S,S )- tartaric anhydride with acetals of N-alkylaminoacetaldehyde gave new chiral auxiliaries (1 R ,5 S ,7 R )- and (1 S ,5 R ,7 S )-3-alkyl-2-oxo-3-aza-6,8-dioxabicyclo[3.2.1]octane-7-carbpxu;oc (RADO(alkyl)-X and SADO(alkyl)-X) derivatives, respectively. The latter could be used to generate the corresponding 1-cyanovinyl esters that add to furan to give readily crystallizable, optically pure Diels-Alder adducts. The method was illustrated by application to the synthesis of (−)-(1 S ,4 S )-7-oxabicyclo[2.2.1]-hept-5-en-2-one.
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Rocha C. S., Vogel P. New chiral auxiliaries and new optically pure ketene equivalents derived from tartaric acids. Improved synthesis of (−)-7-oxabicyclo[2.2.1]hept-5-en-2-one. // Tetrahedron Asymmetry. 1990. Vol. 1. No. 10. pp. 729-736.
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Rocha C. S., Vogel P. New chiral auxiliaries and new optically pure ketene equivalents derived from tartaric acids. Improved synthesis of (−)-7-oxabicyclo[2.2.1]hept-5-en-2-one. // Tetrahedron Asymmetry. 1990. Vol. 1. No. 10. pp. 729-736.
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TY - JOUR
DO - 10.1016/s0957-4166(00)82385-x
UR - https://doi.org/10.1016/s0957-4166(00)82385-x
TI - New chiral auxiliaries and new optically pure ketene equivalents derived from tartaric acids. Improved synthesis of (−)-7-oxabicyclo[2.2.1]hept-5-en-2-one.
T2 - Tetrahedron Asymmetry
AU - Rocha, Cristina S
AU - Vogel, P.
PY - 1990
DA - 1990/01/01
PB - Elsevier
SP - 729-736
IS - 10
VL - 1
SN - 0957-4166
SN - 1362-511X
ER -
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BibTex (up to 50 authors)
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@article{1990_Rocha,
author = {Cristina S Rocha and P. Vogel},
title = {New chiral auxiliaries and new optically pure ketene equivalents derived from tartaric acids. Improved synthesis of (−)-7-oxabicyclo[2.2.1]hept-5-en-2-one.},
journal = {Tetrahedron Asymmetry},
year = {1990},
volume = {1},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/s0957-4166(00)82385-x},
number = {10},
pages = {729--736},
doi = {10.1016/s0957-4166(00)82385-x}
}
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MLA
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Rocha, Cristina S., and P. Vogel. “New chiral auxiliaries and new optically pure ketene equivalents derived from tartaric acids. Improved synthesis of (−)-7-oxabicyclo[2.2.1]hept-5-en-2-one..” Tetrahedron Asymmetry, vol. 1, no. 10, Jan. 1990, pp. 729-736. https://doi.org/10.1016/s0957-4166(00)82385-x.