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Stereoselective nitrile oxide cycloadditions to chiral allyl ethers and alcohols. The inside alkoxy effect
Abstract
We have studied the stereoselectivities of nitrile oxide cycloadditions to a variety of alkenes substituted by chiral allylic ether and alcohol units.2-8 The experimental results, combined with theoretical studies, lead us to propose that allylic ethers adopt the inside position and alkyl substituents prefer the sterically less crowded anti conformation in transition states for these electrophilic cycloadditions. This “inside alkoxy” effect is useful for predicting stereoselectivities of a host of electrophilic reactions with chiral allylic ethers.
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Cited by
Studer, A., Hadida, S., Ferritto, R., Kim, S.-Y., Jeger, P., Wipf, P., & Curran, D. P. (1997) · Science · doi:10.1126/science.275.5301.823 · Cited by 470
Metadata
- Authors
- Houk, K. N., Moses, S. R., Wu, Y. D., Rondan, N. G., Jager, V., Schohe, R., & Fronczek, F. R.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1984-06
- Volume
- 106
- Issue
- 13
- Pages
- 3880-3882
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2030862186
- Cited by
- 274
- References
- 0
- FWCI
- 15.00
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Stereoselective nitrile oxide cycloadditions to chiral allyl ethers and alcohols. The inside alkoxy effect. https://app.cochat.ai/papers/10.1021/ja00325a040
- The paper
- Houk, K. N., Moses, S. R., Wu, Y. D., Rondan, N. G., Jager, V., Schohe, R., & Fronczek, F. R. (1984). Stereoselective nitrile oxide cycloadditions to chiral allyl ethers and alcohols. The inside alkoxy effect. Journal of the American Chemical Society. https://doi.org/10.1021/ja00325a040
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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