ORGN 364 |
| The asymmetric synthesis of b-TMS-homopropargylic amines 4 through the addition of allenylborane 3 to N-H aldimines will be presented and discussed. The insertion of TMSCHN2 into enantiomerically pure B-alkynyl-10-TMS-9-borabicyclo[3.3.2]decanes 2 followed by a sterically driven 1,3-suprafacial borotropic shift proceeds with complete stereospecificity to produce reagents 3 as a single compound in diastereomerically and enantiomerically pure form. Reagents 3 give 4 (51- 85%, syn/anti >99%, 94-99% ee) permitting the recovery of 1.
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Asymmetric Reactions and Syntheses
1:00 PM-5:00 PM, Tuesday, March 27, 2007 McCormick Place East -- Room E351, Level 3, Oral
Division of Organic Chemistry |
