Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin,4-hydroxy-2,6-bis(triphenylsilyl)-, 4-oxide, (11bR)-

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CAS: 791616-55-2
MF: C56H41O4Si2P
MW: 865.06714
Synonyms: Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin,4-hydroxy-2,6-bis(triphenylsilyl)-, 4-oxide, (11bR)-

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Shi-Wei Luo

University of Science and Technology of China
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Co-reporter: Feng Shi, Gui-Juan Xing, Zhong-Lin Tao, Shi-Wei Luo, Shu-Jiang Tu, and Liu-Zhu Gong
pp: 6970-6979
Publication Date(Web):July 24, 2012
DOI: 10.1021/jo301174g
An organocatalytic asymmetric three-component Povarov reaction involving 2-hydroxystyrenes has been established to provide an efficient method to access structurally diverse cis-disubstituted tetrahydroquinolines in high stereoselectivities of up to >99:1 dr and 97% ee. This protocol also provides an easy access to tetrahydroquinolines with chiral quaternary stereocenters upon using α-alkyl 2-hydroxystyrenes as substrates. The theoretical studies revealed that the Povarov reaction proceeded through a sequential vinylogous Mannich reaction and an intramolecular Friedel–Crafts reaction, wherein the phosphoric acid acted as bifunctional catalyst to activate 2-hydroxystyrene and aldimine simultaneously.

Shang-Dong Yang

Chinese Academy of Sciences
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Wenhao Hu

East China Normal University
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Robert R. Knowles

Princeton University
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Yungui Peng

Southwest University
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Li-Hua Gan

Southwest University
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Magnus Rueping

RWTH Aachen University
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Svetlana B. Tsogoeva

University of Erlangen-Nuremberg
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Masahiro Terada

Tohoku University
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Yoshitane Imai

Kinki University
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