Chiral-Auxiliary-Induced Diastereoselectivity in the [4 + 2] Cycloadditions of Optically Active 2,2-Dimethyloxazolidine Derivatives of Sorbic Acid:  A Model Study with Singlet Oxygen as the Smallest Dienophile

1998 ◽  
Vol 120 (17) ◽  
pp. 4091-4093 ◽  
Author(s):  
Waldemar Adam ◽  
Markus Güthlein ◽  
E.-M. Peters ◽  
Karl Peters ◽  
Thomas Wirth
Keyword(s):  
Singlet Oxygen ◽  
Sorbic Acid ◽  
Optically Active ◽  
Chiral Auxiliary ◽  
Model Study ◽  
Derivatives Of

Stereoselective and enantioselective synthesis of five-membered rings via conjugate additions of allylsulfone carbanions

2000 ◽  
Vol 72 (9) ◽  
pp. 1671-1683 ◽  
Author(s):  
Alfred Hassner ◽  
Eugene Ghera ◽  
Tamar Yechezkel ◽  
Victoria Kleiman ◽  
Thiagarajan Balasubramanian ◽  
...  
Keyword(s):  
Membered Ring ◽  
Optically Active ◽  
Enantioselective Synthesis ◽  
Ring Closure ◽  
Chiral Auxiliary ◽  
Asymmetric Induction ◽  
Conjugate Additions ◽  
Derivatives Of ◽  
The Michael Addition ◽  
High Stereoselectivity

This lecture describes some of our studies of lithio derivatives of allyl sulfone carbanions which add α-regioselectively as well as anti diastereoselectively to Michael acceptor olefins. This can be ascribed to chelation in the Michael addition step. When the reaction leads to subsequent ring closure by using a bromoallyl sulfone, the latter acts as a methylenemethane synthon in a (3+2) Michael-initiated ring closure, affording highly functionalized cyclopentane derivatives. Such additions proceed with high stereoselectivity and with asymmetric induction leading to nonracemic substituted cyclopentanones. Additions of allyl sulfone carbanions also proceed stereoselectively to C=N systems containing a chiral auxiliary on N. These can be used in the synthesis of optically active five- and six-membered ring N-heterocycles. Furthermore, chiral groups on the allyl sulfone moiety can induce significant remote asymmetric induction, made possible by the presence of an aromatic π-system which promotes intramolecular chelation to the Li cation.

scholarly journals Enantiopure Derivatives of Aza-Baylis-Hillman Adducts by Subsequent SN′-SN′ Reactions of Acylcarbamates Bearing a Chiral Auxiliary

Molecules ◽  
2009 ◽  
Vol 14 (8) ◽  
pp. 2824-2835 ◽  
Author(s):  
Gianluca Martelli ◽  
Eleonora Marcucci ◽  
Mario Orena ◽  
Samuele Rinaldi
Keyword(s):  
Chiral Auxiliary ◽  
Derivatives Of

Novel optically active organometallic derivatives of fullerenes with non-central types of chirality in addends: synthetic and CD studies

2009 ◽  
Vol 50 (38) ◽  
pp. 5347-5350 ◽  
Author(s):  
Viatcheslav I. Sokolov ◽  
Vasily V. Bashilov ◽  
Fedor M. Dolgushin ◽  
Natalya V. Abramova ◽  
Kyrill K. Babievsky ◽  
...  
Keyword(s):  
Optically Active ◽  
Cd Studies ◽  
Derivatives Of

ChemInform Abstract: REACTIVITY OF ORGANOTIN COMPOUNDS. XII. SYNTHESIS OF OPTICALLY ACTIVE INDENYL L DERIVATIVES OF TIN

1978 ◽  
Vol 9 (27) ◽  
Author(s):  
A. N. KASHIN ◽  
V. A. KHUTORYANSKII ◽  
V. N. BAKUNIN ◽  
I. P. BELETSKAYA ◽  
O. A. REUTOV
Keyword(s):  
Optically Active ◽  
Organotin Compounds ◽  
Derivatives Of

ChemInform Abstract: STEREOCHEMICAL STUDIES OF ADRENERGIC DRUGS. OPTICALLY ACTIVE DERIVATIVES OF IMIDAZOLINES

1977 ◽  
Vol 8 (16) ◽  
pp. no-no
Author(s):  
D. D. MILLER ◽  
F. L. HSU ◽  
R. R. JUN. RUFFOLO ◽  
P. N. PATIL
Keyword(s):  
Optically Active ◽  
Adrenergic Drugs ◽  
Derivatives Of

Camphoryl sulfide as a chiral auxiliary and a mediator for one-step synthesis of optically active 1,2-diaryloxiranes

1989 ◽  
Vol 54 (17) ◽  
pp. 4222-4224 ◽  
Author(s):  
Naomichi Furukawa ◽  
Yasushi Sugihara ◽  
Hisashi Fujihara
Keyword(s):  
Optically Active ◽  
Chiral Auxiliary ◽  
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