Premium
Chirale Tripod‐Liganden: Ein neuer Syntheseweg zu chiralen, C 1 ‐symmetrischen Neopentyltris(phosphan)‐Liganden H 3 CC[CH 2 P(R a ) 2 ][CH 2 P(R b )][CH 2 P(R c ) 2 ]
Author(s) -
Seitz Thomas,
Muth Andreas,
Huttner Gottfried
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19941271004
Subject(s) - chemistry , stereochemistry , tripod (photography) , medicinal chemistry , physics , optics
Chiral Tripod Ligands: A New Synthetic Route to Chiral C 1 ‐symmetrical Neopentyltris(phosphane) Ligands H 3 CC[CH 2 P(R a ) 2 ][CH 2 P(R b ) 2 ][CH 2 P(R c ) 2 ] A novel synthesis of chiral tripod ligands H 3 CC[CH 2 P‐(R a )2][CH 2 P(R b ) 2 ][CH 2 P(R c ) 2 ] ( 6 ) containing three different donor groups at their neopentyl backbone is described. The key intermediates H 3 CC[CH 2 P(R a ) 2 ][CH 2 P(R b ) 2 ](CH 2 OH) ( 3 ) are easily obtained starting from pentaglycerine, H 3 CC‐(CH 2 OH) 3 , via the oxetanes ( 2 ) following published procedures. The compounds 3 , after protection of the phosphane functions by BH 3 {formation of H 3 CC[CH 2 P(R a ) 2 BH 3 ][CH 2 P(R b ) 2 BH 3 ](CH 2 0H) ( 4 )} are transformed into the mesylates H 3 CC[CH 2 P(R a ) 2 BH 3 ][CH 2 P‐(R B ) 2 BH 3 ](CH 2 0Ms) ( 5 ), which upon reaction with KP(R c ) 2 and deprotection with morpholine gives fair yields of racemic 6 . The synthetic route described is thus a valuable and efficient alternative to a recently published procedure, based on H 3 CC(CH 2 CI)(CH 2 Br)(CH 2 0S0 2 CF 3 ) as the key intermediate. The compounds 2–6 are obtained in analytically pure form and are fully characterised by spectroscopic data.