Chirality transfer in stereoselective synthesis. A highly stereoselective synthesis of optically active vitamin E side chains

1983 ◽  
Vol 48 (12) ◽  
pp. 2122-2124 ◽  
Author(s):  
Masato Koreeda ◽  
Lindsey Brown
Keyword(s):  
Vitamin E ◽  
Stereoselective Synthesis ◽  
Optically Active ◽  
Side Chains ◽  
Active Vitamin ◽  
Chirality Transfer

New syntheses of optically active vitamin E side chain by chemicoenzymatic approach

Tetrahedron ◽  
1986 ◽  
Vol 42 (24) ◽  
pp. 6687-6692 ◽  
Author(s):  
P. Gramatica ◽  
P. Manitto ◽  
D. Monti ◽  
G. Speranza
Keyword(s):  
Vitamin E ◽  
Optically Active ◽  
Side Chain ◽  
Active Vitamin

1,5-Acyclic stereoselection. The stereocontrolled synthesis of optically active vitamin E fourteen-carbon side chain alcohol

1984 ◽  
Vol 62 (8) ◽  
pp. 1558-1560 ◽  
Author(s):  
Gervais Bérubé ◽  
Pierre Deslongchamps
Keyword(s):  
Vitamin E ◽  
Cyclic Carbonate ◽  
Optically Active ◽  
Diels Alder ◽  
Side Chain ◽  
Active Vitamin ◽  
Chain Alcohol ◽  
Stereocontrolled Synthesis ◽  
Carbon Side Chain ◽  
Vitamine E

The Diels–Alder product 3 was first transformed into the symmetrical nine-membered cyclic carbonate 8. Reaction of 8 with l-(−)-α-methylbenzylamine (12) yielded a mixture of optically active diastereoisomeric urethanes 9a (9, R = H, R′ = C6H5CHCH3NHCO—) and 9b (9, R = C6H5CHCH3NHCO—, R′ = H) which were separated and respectively converted into 11a and 11b. Compounds 11a and 11b were then transformed respectively into the optically active side chain alcohol 2 (R = H) of vitamine E (1).

Stereoselective synthesis of optically active cyclopenta[c]pyridines and tetrahydropyridines

2012 ◽  
Vol 23 (9) ◽  
pp. 662-669 ◽  
Author(s):  
Serdar Sezer ◽  
Yasemin Gümrükçü ◽  
İrem Bakırcı ◽  
M. Yağız Ünver ◽  
Cihangir Tanyeli
Keyword(s):  
Stereoselective Synthesis ◽  
Optically Active

Central–axial–central chirality transfer: asymmetric synthesis of highly substituted indenes bearing a stereogenic quaternary carbon center from optically active propargyl alcohols

2015 ◽  
Vol 51 (2) ◽  
pp. 380-383 ◽  
Author(s):  
Masahiro Egi ◽  
Kaori Shimizu ◽  
Marin Kamiya ◽  
Yuya Ota ◽  
Shuji Akai
Keyword(s):  
Asymmetric Synthesis ◽  
Optically Active ◽  
Quaternary Carbon ◽  
Chirality Transfer ◽  
Propargyl Alcohols

An asymmetric synthesis of highly substituted indenes has been developed via the central–axial–central chirality transfer from optically active propargyl alcohols.

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