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2004
Enantioselective syntheses
O 0031
Rhodium-Catalyzed Enantioselective Conjugate Addition of Organoboronic
Acids to α,β-Unsaturated Sulfones. — The first catalytic procedure for the title reac52- 028 tion
is developed. 2-Pyridyl sulfones are found to be the best substrates, and
CHIRAPHOS to be the optimal chiral ligand. The methodology has a broad scope
regarding both the arylboronic acid and the sulfone substrate. The conjugate addition
products are formed in excellent yields (usually > 90%) and high enantioselectivities
(76—92% e.e.). The efficient elimination of the pyridylsulfonyl group by Julia—Kocienski olefination offers a new approach to the enantioselective synthesis of allylic
substituted alkenes. — (MAULEON, P.; CARRETERO*, J. C.; Org. Lett. 6 (2004)
18, 3195-3198; Dep. Quim. Org., Fac. Cienc., Univ. Auton., Cantoblanco,
E-28049 Madrid, Spain; Eng.) — Steudel
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