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Synlett 2006(16): 2613-2616
DOI: 10.1055/s-2006-951478
DOI: 10.1055/s-2006-951478
LETTER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Diastereoenriched Acetylenic α-N-tert-Butanesulfinamidoalkyl Methoxymethyl Ethers
Weitere Informationen
Publikationsverlauf
Received
23 June 2006
Publikationsdatum:
22. September 2006 (online)
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Abstract
The reaction of racemic 3-alkoxy allenylzinc species (±)-1, derived from (methoxymethyl)[(3-trimethylsilyl)prop-2-ynyl]ether (2), with enantiopure (S S)-N-tert-butanesulfinimines 3 leads to the corresponding diastereomerically enriched acetylenic (S S,3S,4R)-α-N-tert-butanesulfinamidoalkyl methoxymethyl ethers 4 with an excellent stereoselectivity.
Key words
asymmetric synthesis - chiral resolution - diastereoselectivity - transition states - zinc