Abstract
An efficient diastereoselective strategy to access complex structural tetracycles was described through an organocascade quadruple reaction sequence between (E)-2-(3-arylallylidene)-1H-indene-1,3(2H)-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. (Figure presented.).
| Original language | English |
|---|---|
| Pages (from-to) | 1277-1282 |
| Number of pages | 6 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 359 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - 2017 Jan 1 |
Fingerprint
Keywords
- Michael reaction
- indane-1,3-diones
- organocatalysis
- quadruple reaction sequence
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
Cite this
Diastereoselective Synthesis of Functionalized Angularly-Fused Tetracycles via an Organocatalytic Quadruple Reaction Sequence. / Chang, Fu Jie; Gurubrahamam, Ramani; Chen, Kwunmin.
In: Advanced Synthesis and Catalysis, Vol. 359, No. 8, 01.01.2017, p. 1277-1282.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Diastereoselective Synthesis of Functionalized Angularly-Fused Tetracycles via an Organocatalytic Quadruple Reaction Sequence
AU - Chang, Fu Jie
AU - Gurubrahamam, Ramani
AU - Chen, Kwunmin
PY - 2017/1/1
Y1 - 2017/1/1
N2 - An efficient diastereoselective strategy to access complex structural tetracycles was described through an organocascade quadruple reaction sequence between (E)-2-(3-arylallylidene)-1H-indene-1,3(2H)-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. (Figure presented.).
AB - An efficient diastereoselective strategy to access complex structural tetracycles was described through an organocascade quadruple reaction sequence between (E)-2-(3-arylallylidene)-1H-indene-1,3(2H)-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. (Figure presented.).
KW - Michael reaction
KW - indane-1,3-diones
KW - organocatalysis
KW - quadruple reaction sequence
UR - http://www.scopus.com/inward/record.url?scp=85014878252&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85014878252&partnerID=8YFLogxK
U2 - 10.1002/adsc.201700023
DO - 10.1002/adsc.201700023
M3 - Article
AN - SCOPUS:85014878252
VL - 359
SP - 1277
EP - 1282
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 8
ER -