Synthesis of new organotin substituted optically active eleven membered macrodiolides

JIMENA SCOCCIA; JIMENA SCOCCIA, DARÍO C. GERBINO, VICTOR F. TERRAZA, ADRIANA E. ZÚÑIGA, AND JULIO C. PODESTÁ; ADRIANA E. ZÚÑIGA, PABLO M. FIDELIBUS, SANDRA D. MANDOLESI, AND JULIO C. PODESTÁ

TETRAHEDRON-ASYMMETRY

PERGAMON-ELSEVIER SCIENCE LTD

Lugar: Amsterdam; Año: 2016 vol. 27 p. 352 - 360

0957-4166

The synthesis of eight new TADDOL?s like diacrylates and methacrylates is reported. The hydrostannation with triorganotin hydrides 12-14 (R3SnH, R = nBu, Neophyl, Ph) of diesters 6-11 containing different combinations of substituents at carbon C-2 of the dioxolane ring, led to products of macrocyclization, The hydrostannation of diesters 6-9 took place with low diastereoselectivity. The cyclohydrostannation of diacrylate 10 proceeded with complete diastereoselectivity in all cases. The additions to 11 led to four diastereomers, two of them being formed in higher proportion.  In the case of the cyclohydrostannation of diesters 33 and 34, where the four phenyl groups of TADDOL were replaced by 1-naphthyl groups, there is a dramatic increase in the stereoselectivity of the cyclohydrostannation. The hydrostannations with hydrides 12 and 14 of diesters 33 and 34 afforded in all cases only one stannylated macrocycle. Full 1H, 13C, and 119Sn NMR information is reported.