Asymmetric synthesis of (diene)Fe(CO) 3 complexes by a catalytic enantioselective alkylation using dialkylzincs

The reaction of meso-(2, 4-hexadien-1, 6-dial)Fe(CO) 3 complex 1 with several alkylzincs in the presence of 50 mol% of(S)-(+)-diphenyl(1-methylpyrrolidin-2-yl)methanol 6a proceeded with high enantiotopic group- and diastereotopic face-selectivity to give(2R, 6S)-alcohol complexes 2a-c as major produ...

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Bibliographic Details
Published in:Tetrahedron 1998-12, Vol.54 (51), p.15567-15580
Main Authors: Takemoto, Yoshiji, Baba, Yasutaka, Honda, Asami, Nakao, Syusuke, Noguchi, Izumi, Iwata, Chuzo, Tanaka, Tetsuaki, Ibuka, Toshiro
Format: Article
Language:English
Subjects:
Aldehydes
Alkylation
Asymmetric induction
Iron and compounds
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Summary:The reaction of meso-(2, 4-hexadien-1, 6-dial)Fe(CO) 3 complex 1 with several alkylzincs in the presence of 50 mol% of(S)-(+)-diphenyl(1-methylpyrrolidin-2-yl)methanol 6a proceeded with high enantiotopic group- and diastereotopic face-selectivity to give(2R, 6S)-alcohol complexes 2a-c as major products, except in the case with dimethylzinc (>90% de and >98% ee). On the other hand, the methylation of 1 with Me 2Zn proceeded with high enantioselectivity by adding 1.8 equiv. ofTi(Oi-Pr) 4 in the presence of 3 mol% of(S, S)-1, 2-bis(trifluoromethylsulfonamide)cyclohexane 9a (82% de, 96% ee). The enantioselective alkylation was also applied to the kinetic resolution of racemic (sorbic aldehyde)Fe(CO) 3 complex 10. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(98)01010-2