Enantioselective Isoprenylboration Reaction of Aldehydes Catalyzed by a Chiral Phosphoric Acid

The BINOL‐derived chiral phosphoric acid (R)‐TRIP is utilized as an organocatalyst in the asymmetric isoprenylboration reaction of aldehydes, wherein hydrogen‐bond interactions play a key role in the control of enantioselectivity. A wide arrays of enantioenriched dienyl homoallyl alcohols, including...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2019-07, Vol.361 (13), p.3074-3079
Main Authors: Zhang, Yu‐Long, He, Bo‐Jun, Xie, Yi‐Wen, Wang, Yu‐Hao, Wang, Yi‐Long, Shen, Yong‐Cun, Huang, Yi‐Yong
Format: Article
Language:English
Subjects:
Alcohols
Aldehydes
Allylation
Boron reagent
Chemical industry
Chiral phosphoric acid
Cyclohexene
Enantiomers
Isoprenylation
Natural products
Phosphoric acid
Phthalide
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Summary:The BINOL‐derived chiral phosphoric acid (R)‐TRIP is utilized as an organocatalyst in the asymmetric isoprenylboration reaction of aldehydes, wherein hydrogen‐bond interactions play a key role in the control of enantioselectivity. A wide arrays of enantioenriched dienyl homoallyl alcohols, including two natural products (−)‐Ipsdienol and (−)‐Ipsenol, have been successfully constituted. The synthetic application to chiral isoprenylated isobenzofuranone, vinyloxirane and cyclohexene derivatives has also been disclosed.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900203