Scientific Publications

Practical asymmetric synthesis of β-hydroxy γ-amino acids via complimentary aldol reactions.

Publication TypeJournal Article
AuthorsPandya, BA, Dandapani S., Duvall JR, Rowley A., Mulrooney CA, Ryba T., Dombrowski M., Harton M., Young DW, and Marcaurelle LA
AbstractOrthogonally protected chiral β-hydroxy-γ-amino acids can be accessed in >100 g quantities from readily available starting materials and reagents in 3-4 steps. These chiral synthons contain two adjacent stereocenters along with suitably protected functional groups (O-TBS, N-Boc) for downstream reactivity. Implementation of two existing aldol technologies allows rapid access to all possible stereoisomers of 1. The guiding principles during reaction optimization were reaction scalability and operational efficiency. Conversion of the amino acids to a variety of chiral building blocks in 1-2 steps demonstrates their synthetic utility.
Year of Publication2011
JournalTetrahedron
Volume67
Issue34
Pages6131-6137
Date Published (YYYY/MM/DD)2011/08/26
ISSN Number0040-4020
DOI10.1016/j.tet.2011.06.043
PubMedhttp://www.ncbi.nlm.nih.gov/pubmed/21822337?dopt=Abstract