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Stereodivergent Addition of Allylmetal Reagents to Imines Derived from (R)-2,3-Di-O-benzylglyceraldehyde by Appropriate Selection of Metal and Double Stereodifferentiation

✍ Scribed by Ramón Badorrey; Carlos Cativiela; María D. Díaz-de-Villegas; Roberto Díez; José A. Gálvez

Publisher: John Wiley and Sons
Year: 2002
Tongue: English
Weight: 108 KB
Volume: 2002
Category: Article
ISSN: 1434-193X
DOI: 10.1002/1099-0690(200211)2002:22<3763::aid-ejoc3763>3.0.co;2-k

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✦ Synopsis

The addition of allylmetal reagents to N-benzylimines derived from (R)-2,3-di-O-benzylglyceraldehyde has been achieved with high yields and diastereoselectivities. Homoallylamine 2a of syn configuration is obtained preferentially with allylmagnesium bromide, whereas homoallylamine 2a of anti configuration is obtained as the major reaction product with allyl-9-borabicyclo[3.3.1]nonane. Appropriate com- [a

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