Intramolecular [4 + 2] cycloaddition of nitroalkenes for construction of vicinal quaternary stereocenters

Scott E. Denmark; Ramil Y. Baiazitov

doi:10.1021/ol052316n

Intramolecular [4 + 2] cycloaddition of nitroalkenes for construction of vicinal quaternary stereocenters

Scott E. Denmark, Ramil Y. Baiazitov

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

(Chemical Equation Presented) Nitroalkene (E)-1 has been synthesized to test the feasibility of an intramolecular [4 + 2] cycloaddition in a planned synthesis of daphnilactone B. This nitro olefin contains two unique structural features, a nitromethylene lactone and a pendant diene, that combine under the action of SnCl₄ in a highly selective fashion to afford nitronates 2a and 2b. These products represent the correct relationship for the vicinal quaternary stereogenic centers in the core of daphnilactone B.

Original language	English (US)
Pages (from-to)	5617-5620
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	25
DOIs	https://doi.org/10.1021/ol052316n
State	Published - Dec 8 2005

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol052316n

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abstract = "(Chemical Equation Presented) Nitroalkene (E)-1 has been synthesized to test the feasibility of an intramolecular [4 + 2] cycloaddition in a planned synthesis of daphnilactone B. This nitro olefin contains two unique structural features, a nitromethylene lactone and a pendant diene, that combine under the action of SnCl4 in a highly selective fashion to afford nitronates 2a and 2b. These products represent the correct relationship for the vicinal quaternary stereogenic centers in the core of daphnilactone B.",

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AU - Denmark, Scott E.

AU - Baiazitov, Ramil Y.

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Y1 - 2005/12/8

N2 - (Chemical Equation Presented) Nitroalkene (E)-1 has been synthesized to test the feasibility of an intramolecular [4 + 2] cycloaddition in a planned synthesis of daphnilactone B. This nitro olefin contains two unique structural features, a nitromethylene lactone and a pendant diene, that combine under the action of SnCl4 in a highly selective fashion to afford nitronates 2a and 2b. These products represent the correct relationship for the vicinal quaternary stereogenic centers in the core of daphnilactone B.

AB - (Chemical Equation Presented) Nitroalkene (E)-1 has been synthesized to test the feasibility of an intramolecular [4 + 2] cycloaddition in a planned synthesis of daphnilactone B. This nitro olefin contains two unique structural features, a nitromethylene lactone and a pendant diene, that combine under the action of SnCl4 in a highly selective fashion to afford nitronates 2a and 2b. These products represent the correct relationship for the vicinal quaternary stereogenic centers in the core of daphnilactone B.

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JO - Organic Letters

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Intramolecular [4 + 2] cycloaddition of nitroalkenes for construction of vicinal quaternary stereocenters

Abstract

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