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Implication and improvement of stereoselective methylenation of a chiral aldehyde related to total synthesis of the furaquinocins

✍ Scribed by Takeshi Saito; Takao Suzuki; Kazuhiro Takeuchi; Takashi Matsumoto; Keisuke Suzuki

Book ID: 104257108
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 225 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)00746-6

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✦ Synopsis

In relation to the total synthesis of the furaquinocins, stereoselective methylenation of chiral aldehyde 5 is described. The diastereoselectivity of epoxides 6s/6b is high when stabilized sulfur ylides are employed. A double stereo-differentiation phenomenon was observed for the aminosulfoxonium ylide 8: the selectivity with (S)-8 was 30:1, while 5: l with (R)-8.

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