Preparation of new chiral building blocks via asymmetric catalysis

Tetrahedron Letters

Volumn 44, Issue 39, 2003, Pages 7239-7243

  Iwamoto, Mitsuhiro ^a   Kawada, Hatsuo ^a   Tanaka, Tomoyuki ^a   Nakada, Masahisa ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Baker's yeast; CBS catalyst; Enantioselection; Reduction

Indexed keywords

TERPENOID DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; REDUCTION; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0041379817     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.009     Document Type: Article

References (25)

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14. 3: 249.1491, found: 249.1458.
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16. 3: 251.1647, found: 251.1642. Ee was determined by HPLC (254 nm); Dicel Chiral Cell AS-H 0.46 cm φ×25 cm; hexane/isopropanol=14/1; flow rate=0.3 ml/min); retention time: 37.5 min for (R,R)-2a, 41.5 min for (S,S)-2a .
17. 4: 431.0858, found: 431.0859.
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19. The yeast strain showing an oppsite enantiotopic-group selectivity toward similar cyclic diketones has been reported, see: Fuhshuku K., Tomita M., Sugai T. Adv. Synth. Catal. 345:2003;766-774.
20. 3: 199.1334, found: 199.1349. Benzylidene group was not selected for the protection because a new stereogenic center forms in the product, rendering the structure elucidation difficult.
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23. 3: 199.1334, found: 199.1311.
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25. Additives that slow down the second reduction of meso-diketone 3 were not investigated. For such additives, see Ref. 14 and references cited therein.