Face selectivity in Diels-Alder reactions of chiral dienes containing allylic substituents

1988 ◽  
Vol 110 (14) ◽  
pp. 4625-4633 ◽  
Author(s):  
Matthew J. Fisher ◽  
Warren J. Hehre ◽  
Scott D. Kahn ◽  
Larry E. Overman
Keyword(s):  
Diels Alder ◽  
Face Selectivity

Diels–Alder reactions of bicyclic, heteroannular dienones

1992 ◽  
Vol 70 (5) ◽  
pp. 1481-1485 ◽  
Author(s):  
Lucio Minuti ◽  
Roberta Selvaggi ◽  
Aldo Taticchi ◽  
Ming Guo ◽  
Ernest Wenkert
Keyword(s):  
Nmr Spectroscopy ◽  
Structure Analysis ◽  
Aluminum Chloride ◽  
Diels Alder ◽  
Face Selectivity

Aluminum chloride catalyzed Diels–Alder reactions of bicyclic dienones of the hexalone type with 1,3-butadiene, isoprene, (E)-piperylene, and (E)-1-methoxy-1,3-butadiene are described. Structure analysis of the adducts by NMR spectroscopy is presented. The site-, endo–exo-, and face-selectivity of the reactions are discussed.

Asymmetric induction in Diels–Alder reactions of α-alkoxyorthoquinodimethanes

1989 ◽  
Vol 67 (6) ◽  
pp. 1010-1014 ◽  
Author(s):  
James L. Charlton ◽  
Guy L. Plourde ◽  
Glenn H. Penner
Keyword(s):  
Molecular Orbital ◽  
Geometry Optimization ◽  
Diels Alder ◽  
Asymmetric Induction ◽  
Molecular Orbital Calculations ◽  
Cycloaddition Reactions ◽  
Vinyl Ethers ◽  
The Face ◽  
Face Selectivity ◽  
Alkoxy Groups

It has been shown that dienophiles cycloadd selectively to one face of o-quinodimethanes (o-QDMs) bearing chiral α-alkoxy groups. The face selectivity (diastereoselectivity) increases for the series of chiral groups -OCH(Ph)CH3, -OCH(Ph)CH(CH3)2, and -OCH(Ph)C(CH3)3. A similar effect on the face selectivity of the Diels–Alder reactions of chiral alkoxy vinyl ethers for the same series of chiral groups has been noted previously by others. A mechanism has been proposed to explain the face selectivity in the cycloaddition reactions of the alkoxy o-QDMs. Abinitio molecular orbital calculations with geometry optimization on vinyl 1-phenylethyl ether to determine its lowest energy conformations support the proposed mechanism. The absolute stereochemistries of the o-QDM cycloadducts have been determined to verify the predictions of the model. Keywords: o-quinodimethanes, asymmetric, Diels–Alder, cycloaddition.

Effect of allylic substituents on the face selectivity of Diels-Alder reactions of semicyclic dienes

1990 ◽  
Vol 112 (23) ◽  
pp. 8472-8478 ◽  
Author(s):  
S. C. Datta ◽  
R. W. Franck ◽  
R. Tripathy ◽  
G. J. Quigley ◽  
L. Huang ◽  
...  
Keyword(s):  
Diels Alder ◽  
The Face ◽  
Face Selectivity

ChemInform Abstract: Face Selectivity in Diels-Alder Reaction of 4-Substituted Semicyclic Dienes with Dienophiles.

ChemInform ◽  
2010 ◽  
Vol 26 (29) ◽  
pp. no-no
Author(s):  
S. NAGASHIMA ◽  
Y. TAKAOKA ◽  
K. KAWAKAMI ◽  
M. SHIRO ◽  
K. KANEMATSU
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Face Selectivity

The face selectivity directed by an allylic group of a diene in the diels-alder reaction is reversed from that of a dienophile

1985 ◽  
Vol 26 (27) ◽  
pp. 3187-3190 ◽  
Author(s):  
Richard W. Franck ◽  
S. Argade ◽  
C.S. Subramaniam ◽  
Denise M. Frechet
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
The Face ◽  
Face Selectivity

ChemInform Abstract: Chiral 2-Alkoxy-1,3-butadienes: Synthesis and Face-Selectivity in Diels-Alder Reactions.

ChemInform ◽  
2010 ◽  
Vol 27 (4) ◽  
pp. no-no
Author(s):  
J. BARLUENGA ◽  
M. TOMAS ◽  
A. SUAREZ-SOBRINO ◽  
L. A. LOPEZ
Keyword(s):  
Diels Alder ◽  
Face Selectivity
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