Diastereoselective Synthesis of Functionalized Angularly‐Fused Tetracycles  via  an Organocatalytic Quadruple Reaction Sequence | Zendy

Chang FuJie | Zendy; Gurubrahamam Ramani | Zendy; Chen Kwunmin | Zendy

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Diastereoselective Synthesis of Functionalized Angularly‐Fused Tetracycles via an Organocatalytic Quadruple Reaction Sequence

Author(s) -

Chang FuJie,

Gurubrahamam Ramani,

Chen Kwunmin

Publication year - 2017

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201700023

Subject(s) - aldol reaction , chemistry , enantioselective synthesis , yield (engineering) , sequence (biology) , stereochemistry , indene , combinatorial chemistry , catalysis , organic chemistry , biochemistry , materials science , metallurgy

An efficient diastereoselective strategy to access complex structural tetracycles was described through an organocascade quadruple reaction sequence between ( E )‐2‐(3‐arylallylidene)‐1 H ‐indene‐1,3(2 H )‐diones and β‐keto esters. The reaction proceeded through remote 1,6‐addition followed by sequential 1,4‐addition and aldol/aldol reactions to generate angularly‐fused carbocyclic motifs with favourable to excellent yields (up to 94%) and diastereoselectivities (up to >20:1 dr ). An enantioselective organocascade approach was attempted to yield densely functionalized tetracycles containing seven chiral centres including a quaternary centre.

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