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Stereoselection of sterically unbiased Diels–Alder dienes with spiro conjugation

✍ Scribed by Hiroyuki Igarashi; Shigeru Sakamoto; Kentaro Yamaguchi; Tomohiko Ohwada

Book ID: 104231008
Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 106 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)00947-9

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✦ Synopsis

1,3-Cyclopentadienes bearing a fluorene in spiro geometry are nonsterically biased dienes, which can be used to probe the facial selectivities of Diels-Alder reactions. Anti preference of spiro dienes (2 and 3) bearing 2-and 4-nitro and 2-methoxy substituents as Diels-Alder dienes is in striking contrast to facial preference of the related open-chain 5,5-diphenyl-cyclo-1,3-pentadienes.

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