Abstract
Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce γ-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion-π repulsion in the transition state. The utility of this technique is demonstrated in a synthesis of the carbon framework common to the alkaloids martinellic acid and martinelline in five steps.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 3999-4002 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 8 |
| Issue number | 18 |
| DOIs | |
| State | Published - Aug 31 2006 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Molecular Medicine
Cite this
Cycloaddition reactions of imines with 3-thiosuccinic anhydrides : Synthesis of the tricyclic core of martinellic acid. / Ng, Pui Yee; Masse, Craig E.; Shaw, Jared T.
In: Organic Letters, Vol. 8, No. 18, 31.08.2006, p. 3999-4002.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Cycloaddition reactions of imines with 3-thiosuccinic anhydrides
T2 - Synthesis of the tricyclic core of martinellic acid
AU - Ng, Pui Yee
AU - Masse, Craig E.
AU - Shaw, Jared T.
PY - 2006/8/31
Y1 - 2006/8/31
N2 - Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce γ-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion-π repulsion in the transition state. The utility of this technique is demonstrated in a synthesis of the carbon framework common to the alkaloids martinellic acid and martinelline in five steps.
AB - Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce γ-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion-π repulsion in the transition state. The utility of this technique is demonstrated in a synthesis of the carbon framework common to the alkaloids martinellic acid and martinelline in five steps.
UR - http://www.scopus.com/inward/record.url?scp=33748936678&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33748936678&partnerID=8YFLogxK
U2 - 10.1021/ol061473z
DO - 10.1021/ol061473z
M3 - Article
C2 - 16928058
AN - SCOPUS:33748936678
VL - 8
SP - 3999
EP - 4002
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 18
ER -