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Synthesis 2001(16): 2384-2388
DOI: 10.1055/s-2001-18707
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Shi-Kuo Rena, Fei Wanga, Hua-Ni Doua, Chun-An Fana, Lan Heb, Zhen-Lei Songa, Wu-Jiong Xiaa, De-Run Lia, Yan-Xing Jiaa, Xin Lia, 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
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Publication History

Received 2 July 2001
Publication Date:
05 August 2004 (online)

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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