Synthesis of a simple chiral auxiliary derived from levoglucosenone and its application in a Diels–Alder reaction

2009 ◽  
Vol 50 (9) ◽  
pp. 999-1002 ◽  
Author(s):  
María M. Zanardi ◽  
Alejandra G. Suárez
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Auxiliary ◽  
Diels Alder Reaction

ChemInform Abstract: Asymmetric Hetero Diels-Alder Reaction of Nitroso Compounds Utilizing Tartaric Acid Ester as a Chiral Auxiliary.

ChemInform ◽  
2009 ◽  
Vol 40 (18) ◽  
Author(s):  
Hiroki Sakai ◽  
Xia Ding ◽  
Tetsusuke Yoshida ◽  
Shuhei Fujinami ◽  
Yutaka Ukaji ◽  
...  
Keyword(s):  
Tartaric Acid ◽  
Acid Ester ◽  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Auxiliary ◽  
Nitroso Compounds ◽  
Diels Alder Reaction

ChemInform Abstract: Highly Diastereoselective Diels-Alder Reaction Mediated by a Chiral Auxiliary Derived from Amino Indanol: The Role of Conformation on Diastereoselectivity.

ChemInform ◽  
2010 ◽  
Vol 27 (5) ◽  
pp. no-no
Author(s):  
I. W. DAVIES ◽  
C. H. SENANAYAKE ◽  
L. CASTONGUAY ◽  
R. D. LARSEN ◽  
T. R. VERHOEVEN ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Auxiliary ◽  
Diels Alder Reaction

Highly Diastereoselective Diels−Alder Reaction Using a Chiral Auxiliary Derived from Levoglucosenone

2006 ◽  
Vol 8 (7) ◽  
pp. 1487-1490 ◽  
Author(s):  
Ariel M. Sarotti ◽  
Rolando A. Spanevello ◽  
Alejandra G. Suárez
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Auxiliary ◽  
Diels Alder Reaction

Design of a New and Highly Effective Chiral Auxiliary for Diels−Alder Reaction of 1-Aminodiene

2003 ◽  
Vol 68 (25) ◽  
pp. 9809-9812 ◽  
Author(s):  
Raphaël Robiette ◽  
Karima Cheboub-Benchaba ◽  
Daniel Peeters ◽  
Jaqueline Marchand-Brynaert
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Auxiliary ◽  
Diels Alder Reaction ◽  
Highly Effective

Highly diastereoselective diels-alder reaction mediated by a chiral auxiliary derived from amino indanol: The role of conformation on diastereoselectivity

1995 ◽  
Vol 36 (42) ◽  
pp. 7619-7622 ◽  
Author(s):  
Ian W. Davies ◽  
Chris H. Senanayake ◽  
Laurie Castonguay ◽  
Robert D. Larsen ◽  
Thomas R. Verhoeven ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Auxiliary ◽  
Diels Alder Reaction

The Application of 1,2-Oxazinanes as Chiral Cyclic Weinreb Amide-type Auxiliaries Leading to a Three Component One-Pot Reaction

Synthesis ◽  
2021 ◽  
Author(s):  
Gerhard Hilt ◽  
Ludmila Hermann ◽  
Jan Fährmann
Keyword(s):  
Reaction Path ◽  
Organometallic Compounds ◽  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Auxiliary ◽  
One Pot ◽  
Weinreb Amide ◽  
Diels Alder Reaction ◽  
The Stability

1,2-Oxazines were synthesised via a copper-catalysed aerobic acyl nitroso Diels-Alder reaction from 1,4-disubstituted 1,3-dienes and N-Boc-hydroxylamine. From this, 1,2-oxazinanes were received in a novel follow-up reaction path. The stability of several 1,2-oxazines and 1,2-oxazinanes towards organometallic compounds was tested to rate their operability as cyclic chiral Weinreb amide auxiliaries. 3,6-Di-tert-butyl-1,2-oxazinane gave the best results and was introduced as chiral Weinreb amide-type auxiliary to yield chiral α-substituted ketones in a diastereomeric ratio of up to 98:2. The removal of the auxiliary can be performed with BuLi to form unsymmetrical α-chiral ketones. Thereafter, the chiral auxiliary can be re-isolated and purified by sublimation in vacuum.

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