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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
Author(s) -
Badorrey Ramón,
Cativiela Carlos,
DíazdeVillegas María D.,
Díez Roberto,
Gálvez José A.
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200211)2002:22<3763::aid-ejoc3763>3.0.co;2-k
Subject(s) - chemistry , reagent , nonane , bromide , stereochemistry , combinatorial chemistry , metal , organic chemistry , medicinal chemistry
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 combinations of the allylmetal reagent and imines derived from ( R )‐2,3‐di‐ O ‐benzylglyceraldehyde and ( S )‐ or ( R )‐1‐phenylethylamine afforded syn or anti homoallylamines with total stereocontrol through double stereodifferentiation processes. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)