Diastereoselective synthesis of β-heteroaryl syn-α-methyl-β-amino acid derivatives via a double chiral auxiliary approach.
The addition of the SuperQuat enolate to five- and six-membered heterocyclic tert-butyl sulfinimines led to a high syn-selectivity of up to 99:1 in good to excellent yields. The reaction is tentatively proposed to proceed through an open-chain transition state with the presence of an α-heteroatom on the sulfinimine leading to high diastereoselectivities. The adducts were derivatized to β-amino esters and amides in a facile manner.
Neusentis Chemistry, Pfizer Worldwide Research and Development, Eastern Point Road, Groton, Connecticut 06340, USA. jianwei.bian@pfizer.com
Jianwei
J
Bian
David
D
Blakemore
Joseph S
JS
Warmus
Jianmin
J
Sun
Matthew
M
Corbett
Colin R
CR
Rose
Bruce M
BM
Bechle
D000577:Amides / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*
D000577:Amides; D000596:Amino Acids; D007097:Imines; D013452:Sulfonium Compounds; C522016:sulfinimine