Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 3659 - 3664 |
| Number of pages | 6 |
| Journal | Journal of Organic Chemistry |
| Volume | 79 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - 2014 |
Cite this
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Convergent access to polycyclic cyclopentanoids from a,b-unsaturated acid chlorides and alkynes through a reductive coupling, Nazarov cyclization sequence. / Chaplin, Jason Hugh; Jackson, Kristal Emily; White, Jonathan; Flynn, Bernard Luke.
In: Journal of Organic Chemistry, Vol. 79, No. 8, 2014, p. 3659 - 3664.Research output: Contribution to journal › Article › Research › peer-review
TY - JOUR
T1 - Convergent access to polycyclic cyclopentanoids from a,b-unsaturated acid chlorides and alkynes through a reductive coupling, Nazarov cyclization sequence
AU - Chaplin, Jason Hugh
AU - Jackson, Kristal Emily
AU - White, Jonathan
AU - Flynn, Bernard Luke
PY - 2014
Y1 - 2014
N2 - Reductive coupling of a,?-unsaturated acid chlorides A with alkynoyls B provides convergent access to Nazarov cyclization precursors, a-carboxy divinyl ketones C. Cyclization of C gives an intermediate oxyallyl cation intermediate D, which can be trapped with tethered arenes (Ar). The resultant products can be further cyclized through nucleophilic displacement of suitable leaving groups X by tethered OH groups to give lactones (in a subsequent step). Where X is a suitable chiral auxiliary (e.g., oxazolidinone) this strategy affords access to homochiral cyclopentanoids
AB - Reductive coupling of a,?-unsaturated acid chlorides A with alkynoyls B provides convergent access to Nazarov cyclization precursors, a-carboxy divinyl ketones C. Cyclization of C gives an intermediate oxyallyl cation intermediate D, which can be trapped with tethered arenes (Ar). The resultant products can be further cyclized through nucleophilic displacement of suitable leaving groups X by tethered OH groups to give lactones (in a subsequent step). Where X is a suitable chiral auxiliary (e.g., oxazolidinone) this strategy affords access to homochiral cyclopentanoids
UR - http://pubs.acs.org/doi/pdf/10.1021/jo500040b
U2 - 10.1021/jo500040b
DO - 10.1021/jo500040b
M3 - Article
VL - 79
SP - 3659
EP - 3664
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 8
ER -