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2005
Amines
Q 0120
24- 078
Diastereoselective and Enantioselective Rh(I)-Catalyzed Additions of Arylboronic
Acids to N-tert-Butanesulfinyl and N-Diphenylphosphinoyl Aldimines. — The
addition of arylboronic acids to both aliphatic and aromatic optically active N-sulfinyl
imines (I) under optimized conditions affords the corresponding sufinamides with very
high diastereoselectivities. A promising functional group tolerance of the reaction conditions is demonstrated by successful addition of boronic acid (IIe). A one-pot procedure for the synthesis of sulfinamides (III) starting from the aldehyde is exemplified
for compound (IIIe). The enantioselective addition of arylboronic acids to phosphinoyl
imine (VI) also proceeds with high enantioselectivities and yields. Importantly, it is reported that both the N-tert-butanesulfinyl and the N-diphenylphosphinoyl group can be
cleaved under mildly acidic conditions. — (WEIX, D. J.; SHI, Y.; ELLMAN*, J. A.;
J. Am. Chem. Soc. 127 (2005) 4, 1092-1093; Dep. Chem., Univ. Calif., Berkeley,
CA 94720, USA; Eng.) — Klein
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