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Tetrahedron DOI:10.1016/j.tet.2011.06.043

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

Publication TypeJournal Article
Year of Publication2011
AuthorsPandya, BA, Dandapani, S, Duvall, JR, Rowley, A, Mulrooney, CA, Ryba, T, Dombrowski, M, Harton, M, Young, DW, Marcaurelle, LA
JournalTetrahedron
Volume67
Issue34
Pages6131-6137
Date Published2011/08/26
ISSN0040-4020
Abstract

Orthogonally 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.

DOI10.1016/j.tet.2011.06.043
Pubmed

http://www.ncbi.nlm.nih.gov/pubmed/21822337?dopt=Abstract