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Palladium‐Catalyzed Regio‐ and Diastereoselective Tandem Silastannylation/Allyl Addition of Allene Aldehydes and Allene Ketones: Synthesis of cis Cyclopentanols and Cyclohexanols
Author(s) -
Kang SukKu,
Ha YoungHwan,
Ko ByungSoo,
Lim Yoongho,
Jung Jihyun
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020118)41:2<343::aid-anie343>3.0.co;2-1
Subject(s) - allene , tandem , palladium , chemistry , cyclohexanol , catalysis , medicinal chemistry , organic chemistry , materials science , composite material
Two in one : the palladium‐catalyzed regio‐ and diastereoselective silastannylation of allene aldehydes and ketones and the subsequent allyl addition to the carbonyl group gives rise to cis ‐cycloalkanols (see scheme; n = 1, 2; R = H, CH 3 ; X = NTs, O, C(CO 2 Et) 2 , etc.). This tandem process requires a single catalyst and is carried out at a constant temperature.