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Volumn 35, Issue 29, 1994, Pages 5129-5132

Asymmetric dihydroxylation of olefins containing sulfur: Chemoselective oxidation of CC double bonds in the presence of sulfides, 1,3-dithianes, and disulfides

(4) Walsh, Patrick J a Tong Ho, Pui a King, S Bruce a Sharpless, K Barry a

a SCRIPPS RESEARCH INSTITUTE (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DITHIANE DERIVATIVE; ALKENE DERIVATIVE; DISULFIDE; LIGAND; OSMIUM TETRAOXIDE; SULFIDE; SULFUR;

ARTICLE; CHEMICAL BOND; ENANTIOMER; HYDROXYLATION; OXIDATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0028292023 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)77045-6 Document Type: Article

Times cited : (30)

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16
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- Because α,β-unsaturated aldehydes have not proven good substrates for the AD reaction, the high enantioselectivity with this dithiane substrate is promising. Aldehydes protected as acetals have also been shown to be good substrates for the asymmetric dihydroxylation reaction: see
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- 6) δ 142.2, 139.7, 129.7, 129.0, 128.7, 127.9, 127.6, 127.4, 76.2, 75.9, 36.7, 35.0 ppm; HRMS (FAB) [[Truncated]]

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21
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- The reader will no doubt be wondering what the difference is between these osmium-based oxidation systems which so affects the preference for olefin vs. sulfide oxidation or vice versa. A mechanistic rational for this selectivity dichotomy is still elusive, so for the present, we must be content with its synthetic utility which is clear enough.

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