Organobis(heterocuprates), 7 and 8, have been prepared reacting in situ 1,4-dilithiobutane and di-Grignard reagents, obtained from 1,4-dibromobutane and 1,4-dibromobenzene, respectively, with CuSPh and LiCuBr2. The cross-coupling reaction of these di-cuprate reagents with 3-alkyl and 3,3-dialkyl 1-bromo-1,2-dienes (1) provides a general method for selective synthesis of 1,9-decadiynes (5) and 1,4-bis(2-propynyl)benzenes (6), characterized by two identical chiral centres in the alfa position to the triple bonds. The high 1,3-anti stereoselectivity of the coupling process allows us to obtain enantiomerically enriched alfa-omega-diynes 5 and 6 starting from optically active allenic substrates

One pot stereoselective synthesis of chiral α,ω-diynes from bromoallenes and organobis(heterocuprates)

ARONICA, LAURA ANTONELLA;
2002-01-01

Abstract

Organobis(heterocuprates), 7 and 8, have been prepared reacting in situ 1,4-dilithiobutane and di-Grignard reagents, obtained from 1,4-dibromobutane and 1,4-dibromobenzene, respectively, with CuSPh and LiCuBr2. The cross-coupling reaction of these di-cuprate reagents with 3-alkyl and 3,3-dialkyl 1-bromo-1,2-dienes (1) provides a general method for selective synthesis of 1,9-decadiynes (5) and 1,4-bis(2-propynyl)benzenes (6), characterized by two identical chiral centres in the alfa position to the triple bonds. The high 1,3-anti stereoselectivity of the coupling process allows us to obtain enantiomerically enriched alfa-omega-diynes 5 and 6 starting from optically active allenic substrates
2002
Caporusso, ANNA MARIA; Aronica, LAURA ANTONELLA; Geri, R; Gori, M.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/203818
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