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Jao E, Slifer PB, Lalancette R, et al. Addition-Rearrangement of Aryl- and Alkoxysulfonyl Isocyanates with 5-Methyl-Substituted 3,4-Dihydro-2-methoxy-2H-pyrans. Selective Synthesis of Functionalized 2-Piperidones(1). J Org Chem. 1996;61(8):2865-2870doi: 10.1021/jo951868o.
Jao, E., Slifer, P. B., Lalancette, R., & Hall, S. S. (1996). Addition-Rearrangement of Aryl- and Alkoxysulfonyl Isocyanates with 5-Methyl-Substituted 3,4-Dihydro-2-methoxy-2H-pyrans. Selective Synthesis of Functionalized 2-Piperidones(1). The Journal of organic chemistry, 61(8), 2865-2870. https://doi.org/10.1021/jo951868o
Jao, Edwin, et al. "Addition-Rearrangement of Aryl- and Alkoxysulfonyl Isocyanates with 5-Methyl-Substituted 3,4-Dihydro-2-methoxy-2H-pyrans. Selective Synthesis of Functionalized 2-Piperidones(1)." The Journal of organic chemistry vol. 61,8 (1996): 2865-2870. doi: https://doi.org/10.1021/jo951868o
Jao E, Slifer PB, Lalancette R, Hall SS. Addition-Rearrangement of Aryl- and Alkoxysulfonyl Isocyanates with 5-Methyl-Substituted 3,4-Dihydro-2-methoxy-2H-pyrans. Selective Synthesis of Functionalized 2-Piperidones(1). J Org Chem. 1996 Apr 19;61(8):2865-2870. doi: 10.1021/jo951868o. PMID: 11667125.
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J Org Chem. 1996 Apr 19;61(8):2865-2870. doi: 10.1021/jo951868o.

Addition-Rearrangement of Aryl- and Alkoxysulfonyl Isocyanates with 5-Methyl-Substituted 3,4-Dihydro-2-methoxy-2H-pyrans. Selective Synthesis of Functionalized 2-Piperidones(1).

The Journal of organic chemistry

Edwin Jao, Paul B. Slifer, Roger Lalancette, Stan S. Hall

Affiliations

  1. Department of Chemistry, Rutgers University, Newark, New Jersey 07102.

PMID: 11667125 DOI: 10.1021/jo951868o

Abstract

3,4-Dihydro-2-methoxy-5-methyl-2H-pyran and 3,4-dihydro-2-methoxy-5,6-dimethyl-2H-pyran undergo addition-rearrangement reactions with arylsulfonyl isocyanates to generate the corresponding 3-formyl- and 3-acetyl-6-methoxy-3-methyl-1-(arylsulfonyl)-2-piperidones. For example, 3,4-dihydro-2-methoxy-5-methyl-2H-pyran and phenylsulfonyl isocyanate afforded 3-formyl-6-methoxy-3-methyl-1-(phenylsulfonyl)-2-piperidone as a separable trans/cis mixture in high yield. The more reactive phenoxysulfonyl and alkoxysulfonyl isocyanates provided analogous results.

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