Highly enantioselective synthesis of gamma-nitro heteroaromatic ketones in a doubly stereocontrolled manner catalyzed by bifunctional thiourea catalysts based on dehydroabietic amine: a doubly stereocontrolled approach to pyrrolidine carboxylic acids.
A new class of dehydroabietic amine-substituted primary amine-thiourea bifunctional catalysts were designed and synthesized. The doubly stereocontrolled organocatalytic conjugate addition of a variety of heterocycles-bearing ketones to nitroalkenes was investigated for the first time, affording (S)- or (R)-gamma-nitro heteroaromatic ketones with excellent enantioselectivities (up to ee >99%). Furthermore, the nearly optically pure gamma-nitro heteroaromatic ketones can be readily transformed into chiral pyrrolidine carboxylic acids.
Jiang
Xianxing
X
State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou, 730000, China.
Zhang
Yifu
Y
Chan
Albert S C
AS
Wang
Rui
R
D045784:Abietanes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
D045784:Abietanes; D000588:Amines; D002264:Carboxylic Acids; D007659:Ketones; D011759:Pyrrolidines; C013913:dehydroabietic acid; D013890:Thiourea; C032519:pyrrolidine