In:
Advanced Synthesis & Catalysis, Wiley, Vol. 365, No. 9 ( 2023-05-12), p. 1385-1390
Abstract:
A variety of 4‐phosphinylpyrrolidin‐3‐ones was prepared via a [3+2] cycloaddition between aryl aldonitrones and phosphinylallenes. The products were isolated as unique 4,5‐ trans diastereomers, in yields between 47% and 80%, over 23 examples. In the case of chiral racemic allenes, a 2:1 to 4:1 moderate 2,5‐diastereoselectivity was observed. Under the reaction conditions, the cycloadducts directly undergo a rearrangement to afford selectively the corresponding pyrrolidin‐3‐ones. DFT calculations provide some insights into the mechanism, involving the homolytic cleavage of the N−O bond of the cycloadduct. magnified image
Type of Medium:
Online Resource
ISSN:
1615-4150
,
1615-4169
DOI:
10.1002/adsc.202201386
Language:
English
Publisher:
Wiley
Publication Date:
2023
detail.hit.zdb_id:
2041384-1
detail.hit.zdb_id:
2033084-4
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