title: Practical asymmetric synthesis of β-hydroxy γ-amino acids via complimentary aldol reactions.
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.
authors.affiliation: Chemical Biology Platform, The Broad Institute of MIT and Harvard, 7 Cambridge Center, Cambridge, MA 02142, USA.
authors.forename: Bhaumik A
authors.initials: BA
authors.lastname: Pandya
authors.forename: Sivaraman
authors.initials: S
authors.lastname: Dandapani
authors.forename: Jeremy R
authors.initials: JR
authors.lastname: Duvall
authors.forename: Ann
authors.initials: A
authors.lastname: Rowley
authors.forename: Carol A
authors.initials: CA
authors.lastname: Mulrooney
authors.forename: Troy
authors.initials: T
authors.lastname: Ryba
authors.forename: Michael
authors.initials: M
authors.lastname: Dombrowski
authors.forename: Marie
authors.initials: M
authors.lastname: Harton
authors.forename: Damian W
authors.initials: DW
authors.lastname: Young
authors.forename: Lisa A
authors.initials: LA
authors.lastname: Marcaurelle