Highly stereoselective synthesis of indanes with four stereogenic centers via sequential Michael reaction and [3+2] cycloaddition.
A highly efficient organocatalytic sequential reaction involving Michael addition of bis(phenylsulfonyl)ethylene, in situ condensation and intramolecular nitrone [3+2] cycloaddition with a variety of aldehydes and hydroxyamines to afford a single diastereomer of indanes with four stereogenic centers in excellent yields and stereoselectivities was developed.
Chua
Pei Juan
PJ
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371, Singapore.
Tan
Bin
B
Yang
Limin
L
Zeng
Xiaofei
X
Zhu
Di
D
Zhong
Guofu
G
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D005030:Ethylenes / Q000138:chemical synthesis / Q000737:chemistry; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry
C551485:1,1-bis(phenylsulfonyl)ethylene; D000447:Aldehydes; D005030:Ethylenes; D007189:Indans; D013438:Sulfhydryl Compounds