(1R,3R,4S)-1-benzyl-3-(tert-butyldimethylsilyloxy)-4-(hydroxymethyl)pyrrolidine-borane: novel B-H...H-O hydrogen bonding.
The absolute configuration of the title cis-(1R,3R,4S)-pyrrolidine-borane complex, C(18)H(34)BNO(2)Si, was confirmed. Together with the related trans isomers (3S,4S) and (3R,4R), it was obtained unexpectedly from the BH(3) x SMe(2) reduction of the corresponding chiral (3R,4R)-lactam precursor. The phenyl ring is disordered over two conformations in the ratio 0.65:0.35. The crystallographic packing is dominated by the rarely found donor-acceptor hydroxy-borane O-H...H-B hydrogen bonds.
Gainsford
Graeme J
GJ
Carbohydrate Chemistry Group, Industrial Research Limited, PO Box 31-310, Lower Hutt, New Zealand 5010. g.gainsford@irl.cri.nz
Luxenburger
Andreas
A
Woolhouse
Anthony D
AD
D001880:Boranes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007769:Lactams / Q000737:chemistry*; D008968:Molecular Conformation; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C552270:1-benzyl-3-(tert-butyldimethylsilyloxy)-4-(hydroxymethyl)pyrrolidineborane; D001880:Boranes; D007769:Lactams; D011759:Pyrrolidines