Abstract
An efficient organocatalytic cascade reaction for the synthesis of the bicyclo[3.3.1]nonan-9-one skeleton is reported. The cascade reaction proceeds smoothly between prochiral 4-substituted cyclohexanones and (E)-2-(3-arylallylidene)-indene-1,3-diones involving a 1,6-/γ-protonation/1,4-addition sequence to construct bicyclic products that contain five stereogenic centers in good to high chemical yields and excellent diastereo- and enantioselectivity (up to >20:1 dr and 97% ee) in the presence of a thioether-linked l-prolinol-camphor-derived organocatalyst at ambient temperature. An interesting organocatalytic three-component triple cascade reaction has been performed to produce a bicyclo[2.2.2]octan-2-one in a favorable chemical yield and stereoselectivity (>19:1 dr and 97% ee) starting from 1,3-indanedione, an enal, and cyclohexenone in the presence of a primary amine organocatalyst. (Figure presented.).
| Original language | English |
|---|---|
| Pages (from-to) | 3005-3013 |
| Number of pages | 9 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 359 |
| Issue number | 17 |
| DOIs | |
| Publication status | Published - 2017 Sep 4 |
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Keywords
- bicyclic compounds
- cascade reaction
- enantioselectivity
- organocatalysis
- vinylogous process
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
Cite this
Organocascade Synthesis of Bicyclo[3.3.1]nonan-9-ones Initiated by an Unusual 1,6-Addition of Cyclohexanones to (E)-2-(3-Arylallylidene)-1H-indene-1,3(2H)-diones. / Wang, De Chih; Huang, Pin Han; Huang, Wan Wun; Cheng, You Song; Chen, Kwunmin.
In: Advanced Synthesis and Catalysis, Vol. 359, No. 17, 04.09.2017, p. 3005-3013.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Organocascade Synthesis of Bicyclo[3.3.1]nonan-9-ones Initiated by an Unusual 1,6-Addition of Cyclohexanones to (E)-2-(3-Arylallylidene)-1H-indene-1,3(2H)-diones
AU - Wang, De Chih
AU - Huang, Pin Han
AU - Huang, Wan Wun
AU - Cheng, You Song
AU - Chen, Kwunmin
PY - 2017/9/4
Y1 - 2017/9/4
N2 - An efficient organocatalytic cascade reaction for the synthesis of the bicyclo[3.3.1]nonan-9-one skeleton is reported. The cascade reaction proceeds smoothly between prochiral 4-substituted cyclohexanones and (E)-2-(3-arylallylidene)-indene-1,3-diones involving a 1,6-/γ-protonation/1,4-addition sequence to construct bicyclic products that contain five stereogenic centers in good to high chemical yields and excellent diastereo- and enantioselectivity (up to >20:1 dr and 97% ee) in the presence of a thioether-linked l-prolinol-camphor-derived organocatalyst at ambient temperature. An interesting organocatalytic three-component triple cascade reaction has been performed to produce a bicyclo[2.2.2]octan-2-one in a favorable chemical yield and stereoselectivity (>19:1 dr and 97% ee) starting from 1,3-indanedione, an enal, and cyclohexenone in the presence of a primary amine organocatalyst. (Figure presented.).
AB - An efficient organocatalytic cascade reaction for the synthesis of the bicyclo[3.3.1]nonan-9-one skeleton is reported. The cascade reaction proceeds smoothly between prochiral 4-substituted cyclohexanones and (E)-2-(3-arylallylidene)-indene-1,3-diones involving a 1,6-/γ-protonation/1,4-addition sequence to construct bicyclic products that contain five stereogenic centers in good to high chemical yields and excellent diastereo- and enantioselectivity (up to >20:1 dr and 97% ee) in the presence of a thioether-linked l-prolinol-camphor-derived organocatalyst at ambient temperature. An interesting organocatalytic three-component triple cascade reaction has been performed to produce a bicyclo[2.2.2]octan-2-one in a favorable chemical yield and stereoselectivity (>19:1 dr and 97% ee) starting from 1,3-indanedione, an enal, and cyclohexenone in the presence of a primary amine organocatalyst. (Figure presented.).
KW - bicyclic compounds
KW - cascade reaction
KW - enantioselectivity
KW - organocatalysis
KW - vinylogous process
UR - http://www.scopus.com/inward/record.url?scp=85028694255&partnerID=8YFLogxK
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U2 - 10.1002/adsc.201700338
DO - 10.1002/adsc.201700338
M3 - Article
AN - SCOPUS:85028694255
VL - 359
SP - 3005
EP - 3013
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 17
ER -