A New One-Pot Synthesis of 2-Quaternary 1,3-Diketones

Shi-Kuo Ren; Fei Wang; Hua-Ni Dou; Chun-An Fan; Lan He; Zhen-Lei Song; Wu-Jiong Xia; De-Run Li; Yan-Xing Jia; Xin Li; Yong-Qiang Tu

doi:10.1055/s-2001-18707

PAPER

A New One-Pot Synthesis of 2-Quaternary 1,3-Diketones

Shi-Kuo Ren^a, Fei Wang^a, Hua-Ni Dou^a, Chun-An Fan^a, Lan He^b, Zhen-Lei Song^a, Wu-Jiong Xia^a, De-Run Li^a, Yan-Xing Jia^a, Xin Li^a, Yong-Qiang Tu*^a
^a Department of Chemistry & National Laboratory of Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China
Fax: +86(931)8912582; e-Mail: tuyq@lzu.edu.cn;
^b Department of Chemistry, Beijing Normal University, Beijing 100875, P. R. China

Abstract

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Abstract

A facile one-pot synthesis of 1,3-diketones with stereogenic quaternary center at C-2 has been developed on the basis of an oxidative-rearrangement of a series of tertiary α-hydroxy epoxides on treatment with pyridinium chlorochromate (PCC). A possible mechanism is also discussed.

Key words

1,3-diketones - quaternary carbon - pyridinium chlorochromate - tertiary α-hydroxy epoxides - oxidative rearrangement

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References

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